Chlorosuccinimide → 6-{[tert-Butyl(dimethyl)silyl]oxy}-3-chloro-1H-indole
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
Product 1
Reagents, catalysts & solvents 1
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.