Water → (5-fluoro-1H-indol-3-yl)-pyridin-4-yl-methanol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-fluoroindole (3.10 g, 23.0 mmol) in methanol (10.0 mL) was added 4-pyridinecarboxaldehyde (2.20 mL, 23.0 mmol), followed by addition of NaOH (2.5 mL, 50%) at 0° C. After stirring for 1 h at 0° C., the reaction Mixture was warmed to room temperature and stirred for 3 h, followed by the addition of water (10.0 mL). The precipitate was collected by filtration and dried under vacuum to afford 5.2 g (93%) of a light yellow solid: mp 171-173° C.; 1H NMR (DMSO, 400 MHz), 5.85 (d, 1H), 5.93 (d, 1H), 6.86-7.34 (m, 4H), 7.43 (dd, 2H), 8.48 (dd, 2H), 11.09 (br s, 1H); MS (EI) m/z 242 (M+); HRMS calcd for C14H12FN2O [M+H] 243.09337, found 243.09576.

Provenance & Evidence