2-Methyl-2-butene → HCID 86698618, compound

Participants

Reaction Steps

To a solution of 6-chloro-5-[4-(oxetan-3-yloxy)phenyl]-1H-indole-3-carbaldehyde (100 mg, 0.34 mmol) in acetonitrile (4 mL) was added tert-butanol (4 mL), water (4 mL) and 2-methyl-2-butene (2.52 mL). The reaction mixture was stirred for 2 minutes and treated with sodium chlorite (620 mg, 9.25 mmol) and sodium phosphate monobasic (1.45 g, 9.29 mmol). The mixture was stirred at room temperature for 17 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 (2×10 mL), dried over Na2SO4 and concentrated in vacuo to give a residue, which was purified by prep-HPLC to give 6-chloro-5-[4-(oxetan-3-yloxy)phenyl]-1H-indole-3-carboxylic acid (45 mg, 42%) as an off-white solid. MS (ES+) 343.9 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 11.32 (s, 1H), 8.07 (s, 1H), 7.92 (s, 1H), 7.62 (s, 1H), 7.35 (d, 2H), 6.87 (d, 2H), 5.35-5.32 (m, 1H), 4.97-4.94 (m, 2H), 4.61-4.58 (m, 2H).

Provenance & Evidence