3-Fluorobenzyl bromide → HCID 59161310, compound

Participants

Reaction Conditions

Reaction Steps

Combine (6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-carbamic acid methyl ester (460 mg, 1.7 mmol) and anhydrous dimethylformamide (15 mL) under nitrogen. Chill the mixture to 0° C. and add potassium bis(trimethylsilyl)amide (0.5M toluene solution, 3.4 mL, 1.7 mmol). Stir the resulting mixture for 30 minutes, then add 3-fluorobenzyl bromide (210 μL, 1.7 mmol) and stir the reaction mixture for 4 h allowing slow warming to room temperature. Quench the reaction with water (50 mL) and extract the product with ethyl acetate (2×50 mL). Dry the combined extracts with magnesium sulfate and concentrate in vacuo. Purify the product via flash chromatography (25% ethyl acetate/hexanes isocratic) to afford 475 mg (74%) of a white solid. LCMS (Method E): 100% (m/z) 378 (M+1, APCI-pos); 1H NMR (DMSO, 400 MHz): δ 11.33 (s, 1H), 7.85 (s, 1H), 7.46 (d, 1H, J=7.9 Hz), 7.39-7.27 (m, 7H), 5.03 (q, 2H, J=8.8 Hz), 3.87-3.75 (m, 1H), 3.87-3.75 (m, 1H), 2.96 (dd, 1H, J=15.2, 5.1 Hz), 2.85-2.77 (m, 2H), 2.55-2.49 (m, 1H), 2.07-1.97 (m, 1H), 1.85-1.71 (m, 1H).

Provenance & Evidence