Ethyl Acetate → 5-(3,5-Dimethylisoxazol-4-yl)-3-hydroxy-3-phenylindolin-2-one

Participants

Reaction Steps

Under N2, a mixture of 3,5-dimethylisoxazol-4-ylboronic acid (28 g, 200 mmol, 1.5 eq), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) (4.5 g, 6.1 mmol, 0.05 eq), 5-bromo-3-hydroxy-3-phenylindolin-2-one (40 g, 132 mmol, 1.0 eq) and Na2CO3 (45 g, 425 mmol, 3.2 eq) in dioxane/H2O (500 mL/120 mL) was heated to reflux for 5 h. After cooled down, 500 mL EA was added, the mixture was filtered through a pad of celite, the filter was washed with brine (500 mL×2), dried over Na2SO4, concentrated, purified by sili-gel to give product 27.7 g (yield, 65.6%). 1H NMR (400 MHz, DMSO-d6): δH 10.51 (s, 1H), 7.25-7.34 (m, 6H), 7.10 (m, 1H), 6.99-7.01 (d, 1H, J=8.0 Hz), 6.72 (s, 1H), 2.33 (s, 31H), 2.16 (s, 3H). MS (ESI) m/e [M+1]+ 321.

Provenance & Evidence