Ethyl Acetate → HCID 86282448, compound

Participants

Reaction Steps

A mixture of 3,5-dimethylisoxazol-4-ylboronic acid (120 g, 851 mmol, 2.0 eq), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) (10 g, 13.7 mmol, 0.03 eq), 5-bromo-3-(4-fluorophenyl)-3-hydroxyindolin-2-one (136 g, 422 mmol, 1.0 eq) and Na2CO3 (100 g, 943 mmol, 2.2 eq) were dissolved in dioxane/H2O (800 mL/200 mL), which was heated to reflux for 5 h under N2 atmosphere. After cooled to room temperature, IL EA was added, the mixture was filtered through a pad of celite, the filter was washed with brine (1 L×2), dried over Na2SO4, concentrated, which was purified by silical gel to give 70 g yellow solid (yield, 49%). 1H NMR (400 MHz, DMSO-d6): δH 10.56 (s, 1H), 7.31-7.33 (m, 2H), 6.93 (d, J=8.0 Hz, 1H), 4.27-4.35 (m, 4H), 2.35 (s, 3H), 2.18 (s, 3H). MS (ESI) m/e [M+1]+ 339.

Provenance & Evidence