Sodium Sulfite → 5-{4-[1-(hydroxymethyl)cyclopropyl]phenyl}-6-methyl-1H-indole-3-carboxylic acid

Participants

Reaction Steps

To a solution of 5-{4-[1-(hydroxymethyl)cyclopropyl]phenyl}-6-methyl-1H-indole-3-carbaldehyde (50 mg, 0.164 mmol) in acetonitrile (3.3 mL), t-butanol (3.3 mL) and 2-methyl-2-butene (2.2 mL) was added a solution of sodium chlorite (221 mg, 3.28 mmol) and sodium dihydrogen phosphate (452 mg, 3.28 mol) in water (3.3 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. TLC (petroleum ether/EtOAc=1:1) showed most of the starting material was consumed. The reaction was quenched with a solution of sodium sulfite (455 mg, 3.61 mmol) in water (3.0 mL), and extracted with ethyl acetate (20 mL×3). The organic layers were washed with brine (20 mL) and dried over sodium sulfate, filtered and concentrated to give a crude residue, which was purified by reverse phase HPLC to give the title compound (9.3 mg, 18%) as a white solid. MS (AP+) 322.1 (M+1)+. 1H NMR (400 MHz, CD3OD) 7.89 (s, 1H), 7.82 (s, 1H), 7.40 (d, 2H), 7.30 (s, 1H), 7.28 (d, 2H), 3.69 (s, 2H), 2.30 (s, 3H), 0.89 (m, 4H).

Provenance & Evidence