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

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Reaction Steps

Add N-(6-bromo -2,3,4,9-tetrahydro-1H-carbazol-3-yl)isobutyramide (0.25 g, 0.75 mmol) to a suspension of sodium hydride (0.036 g, 0.90 mmol of a 60% dispersion in mineral oil) in DMF (3 mL) and stir for 15 min. Add 3-fluorobenzylbromide (0.10 mL, 0.90 mmol) and stir for 18-72 h. Dilute with water and collect the precipitate by filtration. Purify by silica gel chromatography eluting with 20-100% EtOAc/hexanes gradient to give 0.23 g of a white solid (71%). MS (ES): m/z 443 (M+1), 445 (M+H+2); HPLC: Rt=3.71 min (97.1%); m.p.=177-179° C.

Provenance & Evidence