Chlorosuccinimide → 6-{[tert-Butyl(dimethyl)silyl]oxy}-3-chloro-1H-indole

HRID 1767917Notes

Reaction equation

HRID 1767917 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([Si:13]([CH3:25])([CH3:24])[O:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[CH:20][NH:21]2)=[CH:17][CH:16]=1)([CH3:12])([CH3:11])[CH3:10]>ClCCl>[C:9]([Si:13]([CH3:25])([CH3:24])[O:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([Cl:1])=[CH:20][NH:21]2)=[CH:17][CH:16]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 222508166-((tert-butyldimethylsilyl)oxy)-1H-indole

Product 1

HCID 236145106-{[tert-Butyl(dimethyl)silyl]oxy}-3-chloro-1H-indoleYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-chlorosuccinimide (270 mg, 2 mmol) in dichloromethane (4 ml) is added within 30 min to a solution of 6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (500 mg, 2 mmol) in dichloromethane (10 ml) at 0° C. under an argon atmosphere. The solution was naturally warmed to ambient temperature and stirred for 2 h. Ice water was added and the mixture was extracted two times with tert-butyl methyl ether. The combined extracts were dried over sodium sulfate and the solvent was removed under reduced pressure to give 560 mg (1.98 mmol, 98%) of the title compound as red solid which was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted two times with tert-butyl methyl ether
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ec4cd9626fcc4d6cbec1319c2f8b4e27
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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