Ethyl bromoacetate → Ethyl 2-(4-(5-(3,5-dimethylisoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl) piperazin-1-yl)acetate

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Reaction Steps

To a solution of 5-(3,5-dimethylisoxazol-4-yl)-3-phenyl-3-(piperazin-1-yl)indolin-2-one (194 mg, 0.5 mmol) in DMF (3.0 mL) was added ethyl 2-bromoacetate (417 mg, 2.5 mmol) and potassium carbonate (208 mg, 1.5 mmol), and the mixture was stirred in RT for 0.5 h, and then saturated NH4Cl (10 mL) was added, and the mixture was extracted with CH2Cl2 (2×10 mL), combined the organic phase, dried with Na2SO4, concentrated in vacuo to give crude product. The mixture was purified with chromatography on column using CH2Cl2/MeOH (50/1, v/v) as eluting to afford a white solid (100 mg, 42%). 1H NMR (400 MHz, DMSO-d6): δH 7.52 (d, J=8.0 Hz, 2H), 7.29-7.37 (m, 5H), 7.17 (d, J=8.0 Hz, 1H), 4.65 (s, 2H), 4.16 (q, J=6.8 Hz, 2H), 2.50-2.52 (m, 4H), 2.36 (s, 3H), 218 (s, 3H), 1.17 (t, J=6.8 Hz, 3H). MS (ESI) m/e [M+1]+ 475.

Provenance & Evidence