Ethyl Acetate → 4-Bromo-1-[tert-butyl(dimethyl)silyl]-1H-indole

HRID 1936611Notes

Reaction equation

[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 4-bromo-1H-indole (36 g) in dimethylformamide (80 mL) was treated with a suspension of NaH (60% in mineraloil, 6.9 g) in dimethylformamide (200 mL) at 20° C. After stirring for 30 min the mixture was cooled to −10° C. an treated portionwise with t-butyldimethylsilyl chloride (38 g) followed by stirring for 1 h at room temperature. Standard work-up with ethyl acetate gave and oil which was purified by flash chromatography giving 4-bromo-1-(t-butyldimethylsilyl)-1H-indole (38 g) as a crystalline material.

Workup

stirringby stirring for 1 h at room temperature
customoil which was purified by flash chromatography

Sources & evidence

ORD record: ord-d90956e6597c4c4cba36df69db827f00
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391882B1

Reaction notes

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