(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

Base Information

Chemical Name:(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate
CAS No.:1365533-64-7
Molecular Formula:C₂₉H₄₁BrN₂O₅SSi
Molecular Weight:637.71
Hs Code.:

Synonyms:(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

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Chemical Property of (S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

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Technology Process of (S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

There total 6 articles about (S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: C₂₃H₂₇BrN₂O₅S

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1365533-64-7
(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1016/j.tetlet.2012.01.037

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1365533-64-7
(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: pyridinium hydrobromide perbromide / tetrahydrofuran; chloroform / 1 h / 0 °C

3.1: dmap / dichloromethane / 2 h / 20 °C

4.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 16 h / 0 - 20 °C

4.2: 20 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; pyridinium hydrobromide perbromide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2012.01.037

Reference yield:

: 1365533-62-5
(S)-methyl 3-(2-bromo-1H-indol-3-yl)-2-(p-toluenesulfonamido)propanoate

: 1365533-64-7
(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap / dichloromethane / 2 h / 20 °C

2.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 16 h / 0 - 20 °C

2.2: 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2012.01.037