(Dimethyl sulfide)trihydroboron → HCID 9840637, compound

Participants

Reaction Steps

A mixture of 2-[(9-benzyl-8-fluoro-9H-carbazol-4-yl)oxy]acetonitrile (0.7685 g, 0.0023 mol), dry THF (20 mL) and borane-methyl sulfide (0.71 mL, 0.0075 mol) is stirred at room temperature for 3.5 h. Additional borane-methyl sulfide (0.20 mL, 0.0021 mol) is added and the mixture is stirred overnight. The excess borane is cautiously quenched with methanol and the mixture is concentrated under reduced pressure. Methanol and dichloromethane are added to the residue and the solution is again concentrated under reduced pressure (repeated twice). The solids are then dissolved in methanol/dichloromethane and conc. HCl (3 mL) is added. After the mixture stirred for 50 min, the solvent is removed under reduced pressure and the residue is partitioned between dichloromethane and aq. sodium bicarbonate. The combined organic layers are dried over sodium sulfate and concentrated to dryness. The residue is chromatographed on silica gel (100 mL) using methanol/dichloromethane (2/98 and 4/96) and recrystallized from ethyl acetate/dichloromethane/heptane to give 0.333 g (43%) of the title compound; mp 122.25-123° C.; MS (ESI+) for C21H19FN2O m/z 335.2 (M+H)+; IR (drift) 1602, 1577, 1498, 1456, 1443, 1352, 1337, 1325, 1269, 1254, 1242, 1228, 1141, 792, 736 cm−1; 1H NMR (CDCl3) δ3.30, 4.28, 5.30, 6.70, 7.01, 7.11, 7.22, 7.36, 8.10, NH2 not seen. Anal. Calcd for C21H19FN2O: C, 75.43; H, 5.73; N, 8.38. Found: C, 75.25; H, 5.79; N, 8.28.

Provenance & Evidence