A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates
A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Harjani, Jitendra R. [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2014transfer abstract |
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| Umfang: |
9 |
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| Übergeordnetes Werk: |
Enthalten in: Therapeutic Advances in Pediatric Multiple Sclerosis - 2013, the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry, Amsterdam [u.a.] |
|---|---|
| Übergeordnetes Werk: |
volume:70 ; year:2014 ; number:43 ; day:28 ; month:10 ; pages:8047-8055 ; extent:9 |
| Links: |
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| DOI / URN: |
10.1016/j.tet.2014.08.036 |
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| 245 | 1 | 0 | |a A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates |
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| 520 | |a A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. | ||
| 520 | |a A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. | ||
| 700 | 1 | |a Tang, Andrew X. |4 oth | |
| 700 | 1 | |a Norton, Raymond S. |4 oth | |
| 700 | 1 | |a Baell, Jonathan B. |4 oth | |
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10.1016/j.tet.2014.08.036 doi GBVA2014001000017.pica (DE-627)ELV022363556 (ELSEVIER)S0040-4020(14)01220-4 DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Harjani, Jitendra R. verfasserin aut A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates 2014transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. Tang, Andrew X. oth Norton, Raymond S. oth Baell, Jonathan B. oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:70 year:2014 number:43 day:28 month:10 pages:8047-8055 extent:9 https://doi.org/10.1016/j.tet.2014.08.036 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 70 2014 43 28 1028 8047-8055 9 045F 540 |
| spelling |
10.1016/j.tet.2014.08.036 doi GBVA2014001000017.pica (DE-627)ELV022363556 (ELSEVIER)S0040-4020(14)01220-4 DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Harjani, Jitendra R. verfasserin aut A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates 2014transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. Tang, Andrew X. oth Norton, Raymond S. oth Baell, Jonathan B. oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:70 year:2014 number:43 day:28 month:10 pages:8047-8055 extent:9 https://doi.org/10.1016/j.tet.2014.08.036 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 70 2014 43 28 1028 8047-8055 9 045F 540 |
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10.1016/j.tet.2014.08.036 doi GBVA2014001000017.pica (DE-627)ELV022363556 (ELSEVIER)S0040-4020(14)01220-4 DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Harjani, Jitendra R. verfasserin aut A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates 2014transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. Tang, Andrew X. oth Norton, Raymond S. oth Baell, Jonathan B. oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:70 year:2014 number:43 day:28 month:10 pages:8047-8055 extent:9 https://doi.org/10.1016/j.tet.2014.08.036 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 70 2014 43 28 1028 8047-8055 9 045F 540 |
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10.1016/j.tet.2014.08.036 doi GBVA2014001000017.pica (DE-627)ELV022363556 (ELSEVIER)S0040-4020(14)01220-4 DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Harjani, Jitendra R. verfasserin aut A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates 2014transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. Tang, Andrew X. oth Norton, Raymond S. oth Baell, Jonathan B. oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:70 year:2014 number:43 day:28 month:10 pages:8047-8055 extent:9 https://doi.org/10.1016/j.tet.2014.08.036 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 70 2014 43 28 1028 8047-8055 9 045F 540 |
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10.1016/j.tet.2014.08.036 doi GBVA2014001000017.pica (DE-627)ELV022363556 (ELSEVIER)S0040-4020(14)01220-4 DE-627 ger DE-627 rakwb eng 540 540 DE-600 610 VZ 150 VZ LING DE-30 fid 77.00 bkl Harjani, Jitendra R. verfasserin aut A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates 2014transfer abstract 9 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. Tang, Andrew X. oth Norton, Raymond S. oth Baell, Jonathan B. oth Enthalten in Elsevier Science Therapeutic Advances in Pediatric Multiple Sclerosis 2013 the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry Amsterdam [u.a.] (DE-627)ELV011938943 volume:70 year:2014 number:43 day:28 month:10 pages:8047-8055 extent:9 https://doi.org/10.1016/j.tet.2014.08.036 Volltext GBV_USEFLAG_U GBV_ELV SYSFLAG_U FID-LING 77.00 Psychologie: Allgemeines VZ AR 70 2014 43 28 1028 8047-8055 9 045F 540 |
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a new methodology for the synthesis of 3-amino-1h-indole-2-carboxylates |
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A new methodology for the synthesis of 3-amino-1H-indole-2-carboxylates |
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A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. |
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A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. |
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A new methodology has been developed for the synthesis of 3-amino-1H-indole-2-carboxylates. 2-Aminobenzonitriles were protected as benzyl (2-cyanophenyl)carbamates and converted into corresponding glycinate esters using sodium hydride and bromoacetate esters. Sodium hydride efficiently promotes the addition of the glycinate α-carbon to the cyano group at low temperatures, resulting in the formation of the desired indole core with 3-amino and 2-carboxylate groups. This new methodology uses Pd–C mediated hydrogenolysis with molecular hydrogen, providing neutral conditions for removal of the N-carbamate protecting group. This methodology demonstrates good functional group tolerance towards a variety of substituents in the aromatic ring and ester groups. The overall yield of 3-amino-1H-indole-2-carboxylates obtained by this four-step methodology is at least 30% or higher with yields as high as 50% realised for three of the indoles investigated in this study. |
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