Methyl iodide → HCID 60083716, compound

Participants

Reaction Steps

To a solution of 1-Methyl-1H-indole-2-carboxylic acid {(1S,2R)-2-[(S)-1-cyano-2-(4-hydroxy-phenyl)-ethylcarbamoyl]cyclohexyl}-amide (compound 34, 102 mg, 0.229 mmol) in 3 mL of anhydrous DMF, was added sodium hydride powder (15 mg, 0.594 mmol). The reaction mixture was stirred for 5 min. while gas evolution subsided, then methyl iodide (0.2 mL, 3.1 mmol) was added. The reaction mixture was partitioned between 50 mL of water and 50 mL of ethyl acetate, the separated organic layer was washed with water (2×50 mL), dried with sodium sulfate, filtered, concentrated and purified by column chromatography (50:50, ethyl acetate/hexanes) to give 74 mg (70%) of 1-methyl-1H-indole-2-carboxylic acid ((1S,2R)-2-{[(S)-cyano-(4-methoxy-benzyl)-methyl]-carbamoyl}-cyclohexyl)-amide as a white amorphous solid. MS: 459 (M+H+).

Provenance & Evidence