Acetic Acid → HCID 69096878, compound

Participants

Reaction Steps

To a solution of methyl 6-{hydroxy-[6-methoxy-2-(5-methylthiophen-3-yl)-1H-indol-3-yl]methyl}pyridine-2-carboxylate (335 mg) and a boran-2-picoline complex (92.1 mg) in methanol (1.7 mL) was added acetic acid (1.7 mL), and this mixture was stirred at room temperature for 8 hours. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous sodium hydrogen carbonate solution and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (255 mg). 1H-NMR (CDCl3) δ ppm: 2.48-2.53 (3H, m), 3.85 (3H, s), 4.05 (3H, s), 4.54 (2H, s), 6.74 (1H, dd, J=2.2, 8.6 Hz), 6.88 (1H, d, J=2.2 Hz), 6.96-7.01 (1H, m), 7.17-7.22 (2H, m), 7.29 (1H, d, J=8.6 Hz), 7.62 (1H, t, J=7.8 Hz), 7.93-7.98 (1H, m), 8.01 (1H, br s).

Provenance & Evidence