tert-butyl 6-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-butyl 6-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate
• CAS No.: 854638-56-5
• Molecular Formula: C19H29NO3Si
• Molecular Weight: 347.52400
• Mol file: 854638-56-5.mol

Synonyms:1-(tert-butoxycarbonyl)-6-(tert-butyldimethylsiloxy)indole;

Chemical Property of tert-butyl 6-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate

Chemical Property:

• PSA: 40.46000
• LogP: 5.80850

Purity/Quality:

98% ^*data from raw suppliers

6-[[(1,1-DIMETHYLETHYL)DIMETHYLSILYL]OXY]-1H-INDOLE-1-CARBOXYLIC ACID-1,1-DIMETHYLETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl 6-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate

There total 3 articles about tert-butyl 6-{[tert-butyl(dimethyl)silyl]oxy}-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: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + 6-<<(2,2-dimethylethyl)dimethylsilyl>oxy>indole (106792-41-0) → 6-(tert-butyldimethylsilanyloxy)indole-1-carboxylic acid tert-butyl ester (854638-56-5)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 4h;

Reference yield:

tert-butyldicarbonate (34619-03-9) + 6-<<(2,2-dimethylethyl)dimethylsilyl>oxy>indole (106792-41-0) → 6-(tert-butyldimethylsilanyloxy)indole-1-carboxylic acid tert-butyl ester (854638-56-5)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2011.01.035

Reference yield:

6-hydroxy-1H-indole (2380-86-1) → 6-(tert-butyldimethylsilanyloxy)indole-1-carboxylic acid tert-butyl ester (854638-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1H-imidazole / DMF (N,N-dimethyl-formamide) / 20 h / 20 °C

2: dmap / dichloromethane / 4 h / 20 °C

With 1H-imidazole; dmap; In DMF (N,N-dimethyl-formamide); dichloromethane;

upstream raw materials:

di-tert-butyl dicarbonate

6-<<(2,2-dimethylethyl)dimethylsilyl>oxy>indole

tert-butyldicarbonate

6-hydroxy-1H-indole

Downstream raw materials:

6-(tert-butyldimethylsilanyloxy)indole-1-carboxylic acid tert-butyl ester 2-boronic acid

6-(tert-butyldimethylsiloxymethyl)-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester