Sodium hydride → N-[6-Cyano-9-(2-trifluoromethyl-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide

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Reaction Conditions

Reaction Steps

Suspend sodium hydride (60% in oil, 48 mg, 1.20 mmol) in N,N-dimethylformamide (2.5 mL) and chill to 0° C. Add slowly a solution of N-(6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide (281 mg, 1.00 mmol) in N,N-dimethylformamide (2.5 mL) via syringe, and stir 10 min before warming to ambient temperature for 30 min. Add 2-(trifluoromethyl)benzyl bromide (263 mg, 1.10 mmol) and stir approximately 16 h. Add ethyl acetate (75 mL), wash with water (50 mL) and brine (2×50 mL). Dry the organic phase over magnesium sulfate, filter, and evaporate under reduced pressure. Triturate the residue with 2:1 bexanes:methylene chloride to afford the title compound (333 mg, 76%). MS (ES): m/z 440 (M+1); 1H NMR (300 MHz, CDCl3): δ 7.83 (s, 1H), 7.73 (d, J=7.2 Hz, 1H), 7.39-7.29 (m, 3H), 7.16 (d, J=8.4 Hz, 1H), 6.27 (d, J=7.4 Hz, 1H), 5.53-5.51 (m, 1H), 5.46 (s, 2H), 4.47-4.30 (m, 1H), 3.21-3.15 (m, 1H), 2.67-2.59 (m, 3H), 2.33 (septet, J=6.8 Hz, 1H), 2.16-2.11 (m, 1H), 2.03-1.93 (m, 1H), 1.16 (d, J=6.8 Hz, 3H), 1.15 (d, J=6.8 Hz, 3H); m.p.=222-225° C.

Provenance & Evidence