Sodium borohydride → HCID 86281901, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(5-(3,5-dimethylisoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl)acetate (50 mg, 0.13 mmol) in EtOH (20 mL) was added NaBH4 (49 mg, 1.3 mmol), the reaction mixture was stirred at reflux for 3.0 h. After cooling to 0° C., the reaction was quenched by addition of aq. saturated NH4Cl (2 mL) solution. The mixture was diluted with water (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to yield crude product which were purified on flash column chromatography to afford the title compound as a white solid (10 mg, 22%). 1H NMR (400 MHz, DMSO-d6): δH 10.59 (s, 1H), 7.22-7.35 (m, 7H), 6.98 (d, J=8.0 Hz, 1H), 4.48-4.51 (m, 1H), 3.15-3.17 (m, 2H), 2.44-2.48 (m, 2H), 2.32 (s, 3H), 2.20 (s, 3H). MS (ESI) m/e [M+1]+ 349.

Provenance & Evidence