[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][C:12]#[N:13])=[CH:5][NH:6]2.[H-].[Na+].[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>O1CCCC1>[CH3:16][N:17]([CH3:21])[C:18]([N:6]1[C:7]2[C:3](=[C:2]([Cl:1])[CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:11][C:12]#[N:13])=[CH:5]1)=[O:19]To a solution of (4-chloro-1H-indol-3-yl)-acetonitrile (200 mg, 1.05 mmol) dissolved in anhydrous tetrahydrofuran (5 ml) at 0° C. was added sodium hydride (63 mg, 1.57 mmol, 60% dispersion in mineral oil). After 20 minutes at 0° C., the ice bath was removed and dimethyl carbamyl chloride (0.12 mL, 1.26 mmol) was slowly added. After one hour, the reaction was partitioned between ethyl acetate (100 mL) and saturated sodium chloride solution (2.5 mL). The ethyl acetate extract was dried (anhydrous magnesium sulfate), filtered and concentrated under reduced pressure. The resulting material was purified by flash column chromatography over silica gel eluting with 40% ethyl acetate in hexane to give 4-Chloro-3-cyanomethyl-indole-1-carboxylic acid dimethylamide as a white solid (239 mg, 87%).
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