2-Methyl-2-butene → HCID 71767831, compound

Participants

Reaction Steps

To a solution of 6-fluoro-5-phenyl-1H-indole-3-carbaldehyde (58.0 mg, 0.19 mmol) in MeCN (3 mL), tert-butanol (3 mL) and 2-methyl-2-butene (2 mL, 13.7 mmol) at 0° C. was added a solution of sodium chlorite (253.0 mg, 3.75 mmol) and sodium phosphate monobasic hydrate (585.0 mg, 3.75 mmol) in water (1.5 mL) dropwise. The ice bath was removed and the solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the aqueous residue was extracted with EtOAc (3×15 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude material was purified by prep-HPLC (Boston Symmetrix ODS-H 150*30 mm*5 μm; 26-46% MeCN in water (0.225% formic acid); flow rate: 30 mL/min) to afford the title compound (9.5 mg, 16%) as a white solid. MS (ES+) 324.1 (M−H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.13 (br.s., 1H), 11.95 (s, 1H), 8.04-8.06 (m, 2H), 7.60 (d, J=8.40 Hz, 2H), 7.53 (d, J=6.80 Hz, 2H), 7.38 (d, J=11.20 Hz, 1H), 5.56 (s, 1H), 2.42-2.49 (m, 2H), 2.29-2.36 (m, 2H), 1.93-1.98 (m, 1H), 1.68-1.73 (m, 1H).

Provenance & Evidence