Dichloromethane → 7-Amino-2-methyl-4-[(E)-2-phenylethenyl]-2,3-dihydro-1H-isoindol-1-one

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Reaction Steps

A mixture of 7-amino-4-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one (1.0 g, 4.1 mmol), E-phenylethenylboronic acid (921 mg, 6.22 mmol), potassium carbonate (1.72 g, 12.4 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (169 mg, 0.207 mmol) in 10 mL 1,4-Dioxane and 2.5 mL H2O was irradiated in a microwave reactor at 100° C. for 30 minutes. The crude mixture was partitioned between EtOAc and sat. NaHCO3. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was used in the next step without further purification. MS (ES+): m/z 265.31 (100) [MH+]; HPLC: tR=1.24 min (UPLC, Analytical).

Provenance & Evidence