Tetrahydrofuran → HCID 66787865, compound

Participants

Reaction Conditions

Reaction Steps

To 5-(5-bromo-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one, prepared as described in Example 21, (100 mg, 0.330 mmol) was added potassium cyclopropyltrifluoroborate (50 mg, 0.35 mmol), THF (2 mL), water, (0.66 mL), and tripotassium phosphate (245 mg, 1.155 mmol). The reaction mixture was degassed and placed under an argon atmosphere, and then [1,1′-bis(diphenylphospihino)-ferrocene]-dichloropalladium(II) complexed with dichloromethane (CAS#72287-26-4 13.5 mg, 0.016 mmol) was added. The reaction vessel was sealed and was heated by microwave irradiation at 125° C. for 85 minutes. The reaction mixture was cooled to room temperature, diluted with dichloromethane and filtered through glass wool. The filtrate was further diluted with saturated aqueous sodium bicarbonate and the layers were separated. The aqueous layer was extracted two times with dichloromethane, and 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-dichloromethane, 0 to 100%) to afford 5-(5-cyclopropyl-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one; HRMS: (ESI) m/z 265.1345 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.72-0.89 (m, 2H), 1.03-1.19 (m, 2H), 1.85-2.11 (m, 1H), 3.27 (s, 3H), 3.61 (s, 2H), 6.92 (d, J=8.1 Hz, 1H), 7.39-7.61 (m, 3H), 8.38 (d, J=1.8 Hz, 1H), 8.60 (d, J=2.0 Hz, 1H).

Provenance & Evidence