Sodium Sulfite → 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carboxylic acid

Participants

Reaction Steps

To 5-[4-(azetidin-3-yl)phenyl]-6-chloro-1H-indole-3-carbaldehyde (94 mg, 0.30 mmol) in 2-methyl-2-butene/t-BuOH/H2O (v/v/v=1/1/1, 4 mL) was added sodium dihydrogen phosphate (364 mg, 3.04 mmol) and sodium chlorite (274 mg, 3.04 mmol) at room temperature. The resulting mixture was stirred at room temperature for 24 hours. To the reaction mixture was added sodium sulfite (383 mg, 3.04 mmol), then concentrated in vacuo and purified via reverse phase HPLC to give the title compound (10 mg, 10% yield). 1H NMR (400 MHz, CD3OD) δ 8.03-80.4 (d, 2 H), 7.62 (s, 1 H), 7.48-7.52 (m, 4 H), 4.44-4.48 (m, 2 H), 4.32-4.34 (m, 3 H).

Provenance & Evidence