Aluminium lithium hydride → 5-(3,5-Dimethylisoxazol-4-yl)-3-(4-(2-hydroxyethyl)piperazin-1-yl)-3-phenylindolin-2-one

Participants

Reaction Steps

To a solution of Ethyl 2-(4-(5-(3,5-dimethylisoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl)piperazin-1-yl)acetate (100 mg, 0.21 mmol) in THF (5 mL) was added lithium aluminium tetrahydride (38 mg, 1.05 mmol) at 0° C., the reaction mixture was stirred at RT for 2.0 h. After cooling to 0° C., the reaction was quenched by addition of aq. saturated NH4Cl solution (50 mL). The mixture was diluted with water and extracted with EtOAc (50 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 (30 mg, 33%). 1H NMR (400 MHz, DMSO-d6): δ H 10.69 (s, 1H), 7.22-7.51 (m, 7H), 6.96 (d, J=8.0 Hz, 1H), 4.31 (s, 1H), 3.40-3.45 (m, 2H), 2.13-2.40 (m, 13H), 2.02 (s, 3H). MS (ESI) m/e [M+1]+ 433.

Provenance & Evidence