1-Bromo-3-chloropropane → HCID 20740305, compound

Participants

Reaction Steps

To a stirred solution of 6-chloro-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide from Example 18 (0.428 g, 1.03 mmol) in DMF (3.5 ml) were added NaH (60% dispersion in mineral oil) (0.062 g, 1.54 mmol) at 0° C. The slurry was then stirred at room temperature for one hour followed by the addition of 1-bromo-3-chloropropane (0.13 ml, 1.34 mmol). Reaction was stirred overnight at room temperature and partitioned between 1 N HCl and ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting oil was chromatographed on preparatory silica plates, eluting with 2.5% MeOH/dichloromethane, and yielding 6-chloro-1-(3-chloro-propyl)-1H-indole-2-carboxylic acid [2-(1-cyano-3-methyl-butylcarbamoyl)-cyclohexyl]-amide (0.323 g, 64%). [M+H=492].

Provenance & Evidence