Dichloromethane → HCID 66788680, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-1-methyl-1,3-dihydro-indol-2-one, prepared in a fashion similar as described in Example 39a (CAS#884855-67-8, 1.80 g, 7.5 mmol) in THF (24 mL) was added water (8 mL), tripotassium phosphate (5.57 g, 26.3 mmol), and potassium cyclopropyltrifluoroborate (1.501 g, 10.50 mmol). The reaction mixture was degassed and placed under a nitrogen atmosphere, and then [1,1′-bis(diphenylphosphino)-ferrocene]-dichloropalladium(II) complexed with dichloromethane (CAS#72287-26-4 184 mg, 0.225 mmol) was added. The reaction vessel was sealed and was heated by microwave irradiation at 130° C. for 4 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate and brine and then filtered through a pad of Celite®. The layers of the filtrate were separated and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 100%) to furnish 4-cyclopropyl-1-methyl-1H-indole-2,3-dione; MS: (ES+) m/z 202.4 (M+H)+.

Provenance & Evidence