Tetrahydrofuran → HCID 66793835, compound

Participants

Reaction Conditions

Reaction Steps

To 5-(5-bromo-pyridin-3-yl)-4-chloro-1-methyl-1,3-dihydro-indol-2-one prepared as described in Example 28, (85 mg, 0.25 mmol) was added potassium cyclopropyltrifluoroborate (41 mg, 0.38 mmol), THF (2 mL) water, (0.66 mL), and tripotassium phosphate (187 mg, 0.88 mmol). The reaction mixture was degassed and placed under an argon atmosphere, and then (1,1′-bis(diphenylphosphino)-ferrocenel-dichloropalladium(II) complexed with dichloromethane (CAS#72287-26-4 10.3 mg, 0.013 mmol) was added. The reaction vessel was sealed and was heated by microwave irradiation at 125° C. for 4 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane and 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 through a pad of Celite®, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-dichloromethane, 0 to 100%) to afford 4-chloro-5-(5-cyclopropyl-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one; HRMS: (ESI) m/z 299.0955 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 0.78-0.82 (m, 2H), 1.01-1.18 (m, 2H), 1.94-2.04 (m, 1H), 3.26 (s, 3H), 3.61 (s, 2H), 6.83 (d, J=7.8 Hz, 1H), 7.26-7.31 (m, 1H), 7.44 (br. s., 1H), 8.36-8.54 (m, 2H).

Provenance & Evidence