Ammonium Hydroxide → HCID 86611322, compound

Participants

Reaction Conditions

Reaction Steps

Sodium cyanoborohydride (4.6 g, 73.8 mmol, 3 equiv.) was carefully added to a stirred solution of 1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide (2.4 g, 7.38 mmol, 1 equiv.) in acetic acid (25 mL) over 5 minutes at room temperature. The reaction mixture was stirred for 30 minutes then cooled down to 0° C. and slowly poured onto concentrated ammonium hydroxide (78 mL, d=0.880) at 0° C. The mixture was diluted with water (25 mL) and dichloromethane (25 mL), the organic layer was separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed under vacuum to afford crude 2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide, 1.8 g (73% yield), this material was taken onto the next step without further purification. LC @215 nm; Rt 1.13: 80%, m/z (ES+): 372 (M+H+MeCN).

Provenance & Evidence