反应详情

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).

1. customwas consumed
2. extractionextracted with ethyl acetate (20 mL×3)
3. washThe organic layers were washed with brine (20 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a crude residue, which
8. customwas purified by reverse phase HPLC