反应详情

温度

0 °C

6-fluoro-5-[4-(3-hydroxyoxetan-3-yl)-3-methoxyphenyl]-1H-indole-3-carbaldehyde (86 mg, 0.2534 mmol) was dissolved in MeCN (6 mL) and warm t-butanol (6 mL). 2-methyl-2-butene (4 mL) was then added and cooled to 0° C. Sodium chlorite (342 mg, 5.07 mmol) and sodium dihydrogen phosphate dihydrate (791 mg, 5.07 mmol) were dissolved in water (3 mL). The aqueous solution was added to the organic solution dropwise via addition funnel and the ice bath was removed and the mixture was allowed to warm to room temperature. The reaction was quenched with saturated aqueous sodium sulfite, concentrated to remove the organics and extracted with EtOAc (20 mL×3). The combined organics were washed with brine (20 mL), dried and concentrated to give a crude residue, which was purified by prep HPLC to afford the title compound (7.3 mg, 8.1%) as an off-white solid.

1. additionThe aqueous solution was added to the organic solution dropwise via addition funnel
2. customthe ice bath was removed
3. temperatureto warm to room temperature
4. customThe reaction was quenched with saturated aqueous sodium sulfite
5. concentrationconcentrated
6. customto remove the organics and
7. extractionextracted with EtOAc (20 mL×3)
8. washThe combined organics were washed with brine (20 mL)
9. customdried
10. concentrationconcentrated
11. customto give a crude residue, which
12. customwas purified by prep HPLC