tert-Butyldimethylsilyl chloride → HCID 54418023, compound

HRID 2268979Notes

Reaction equation

HRID 2268979 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH:6]=[C:5]2[CH2:11][C@@H:12]1[CH2:15][CH2:16][CH2:17][N:13]1[CH3:14]

Participants

4

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 158384855-bromo-3-(2-(pyrrolidin-1-yl)ethyl)-1H-indole

Product 1

HCID 54418023HCID 54418023, compound

Procedure

5-Bromo-1-(t-butyldimethylsilyl)-3-(2-pyrrolidin lethyl)indole: (1.02 g, 73%) as a brown oil from 5-bromo-3-(2-pyrrolidinylethyl)-1H-indole (Example 3b, 1.00 g, 3.4 mmol), sodium hexamethyldisilazide (82 mL, 6.82 mmol) and t-butyidimethylsilyl chloride (6.82 mL. 6.82 mmol). 13C NMR (CDCl3): 140.1, 132.9, 129.4, 124.1, 121.5, 116.3, 115.2, 112.7, 6.9, 54.3, 26.3, 25.1, 23.5, 19.5, −3.98.

Sources & evidence

ORD record
ord-08715f8413314ed6bdcd5fed2c79264d
Source dataset
uspto-grants-2001_12
Patent number
US06329390B1

Reaction notes

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