2-Methyl-2-butene → HCID 86698621, compound

Participants

Reaction Steps

To a solution of 6-chloro-5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1H-indole-3-carbaldehyde (130 mg, 0.34 mmol) in acetonitrile (4 mL) was added tert-butanol (4 mL), water (4 mL) and 2-methyl-2-butene (2.76 mL). After stirred for 2 min, sodium chlorite (680 mg, 10.15 mmol) and sodium phosphate monobasic (1.59 mg, 10.19 mmol) were added to the reaction mixture. The mixture was stirred at room temperature for 16 hours. The reaction was quenched with sodium sulfite and the mixture was concentrated in vacuo to give a residue, which was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (2×15 mL), dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by prep-HPLC to give 6-chloro-5-{4-[2-(morpholin-4-yl)ethoxy]phenyl}-1H-indole-3-carboxylic acid (30 mg, 22%) as a yellow solid. MS (ES+) 401.1 (M+H)+. 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 8.02 (s, 1H), 7.98 (s, 1H) 7.57 (s, 1H), 7.39 (d, 2H), 7.04 (d, 2H), 4.31 (m, 2H), 3.83 (m, 4H), 3.17 (m, 2H), 2.96 (m, 4H).

Provenance & Evidence