Dimethylformamide → HCID 86597103, compound

Participants

Reaction Steps

Phosphorous oxychloride (3 mL) was added to anhydrous dimethylformamide (6 mL) and the mixture allowed to stir at room temperature for 15 min. A mixture of 1-(4-benzyloxy-3-fluorophenyl)-2-methyl-1H-indole (1.03 g, 3.1 mmol) in dimethylformamide (10 mL) was added and the mixture heated to 80° C. and held for 18 hr. The reaction mixture was poured onto ice and adjusted to a pH of 7 by the addition of 2 N NaOH. The mixture was extracted with ethyl acetate (2×100 mL), the organic layer washed with water and brine and dried over MgSO4, and evaporated to provide the product as a dark solid. Purification by silica gel chromatography (25% EtOAC-hexanes) provided a white solid (0.84 gr, 76%): mp 166-168-152° C.; 1H NMR (DMSO-d6): δ 2.55 (3H, s), 5.30 (2H, s), 7.04 (1H, d, J=6.9 Hz), 7.19-7.28 (2H, m), 7.23-7.52 (7H, m), 7.44 (2H, dd, J=6.0 Hz, J=1.4 Hz), 7.59 (1H, dd, J=11.7 Hz, J=2.5), 8.17 (1H, dd, J=7.0 Hz, J=1.0), 10.20 (1H, s) Hz; MS m/z (M+H)+ 360: Anal. for C23H18FNO2 (0.1H2O): Calc'd: C, 76.48; H, 5.08; N, 3.88. Found: C, 76.39; H, 4.81; N, 3.69

Provenance & Evidence