Ethyl Acetate → 5'-(3,5-Dimethylisoxazol-4-yl)-7'-methoxyspiro[[1,3]dioxolane-2,3'-indolin]-2'-one

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Reaction Conditions

Reaction Steps

A mixture of 3,5-dimethylisoxazol-4-ylboronic acid (298 mg, 2.1 mmol), dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) (29 mg, 0.14 mmol), 5′-bromo-7′-methoxyspiro[[1,3]dioxolane-2,3′-indolin]-2′-one (210 mg, 0.7 mmol) and Na2CO3 (233 mg, 2.1 mmol) in dioxane (9 mL) and water (2 mL) was heated to 102° C. for 16 h. To the mixture was added EtOAc (50 mL), water (20 mL). The organic layer was separated and washed with water (20 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by column chromatography, using a mixture of 33% EtOAc in dichloromethane as the eluent, to give the desired product as a light brown solid (57 mg, crude, 26%). 1H NMR (400 MHz, DMSO-d6): δH 10.62 (s, 1H), 7.02-7.03 (m, 1H), 6.92-6.93 (m, 1H), 4.26-4.34 (m, 4H), 3.86 (s, 3H), 2.38 (s, 3H), 2.10 (s, 3H). MS (ESI) m/e [M+1]+ 317.

Provenance & Evidence