1,2-Dimethoxyethane → HCID 58255627, compound

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-1-ethyl-1,3-dihydro-indol-2-one (CAS#41192-37-4, 100 mg, 0.42 mmol) was added 3-pyridine boronic acid (CAS#1692-25-7, 50.2 mg, 0.41 mmol), 1,2-dimethoxyethane (2.5 mL), and 2 M aqueous sodium carbonate (0.410 mL, 0.82 mmol). The reaction mixture was degassed and placed under an argon atmosphere, at which time tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.026 mmol)] was added. The reaction vessel was sealed and was heated by microwave irradiation at 100° C. for 45 minutes. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and brine and the layers were separated. The aqueous layer was extracted two times with ethyl acetate, 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-heptane, 10 to 100%) to afford 1-ethyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one; HRMS: (ESI) m/z 239.1190 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (t, J=7.2 Hz, 3H), 3.61 (s, 2H), 3.83 (q, J=7.3 Hz, 2H), 6.96 (d, J=8.1 Hz, 1H), 7.38 (dd, J=7.3, 4.8 Hz, 1H), 7.46-7.57 (m, 2H), 7.78-7.95 (m, 1H), 8.58 (dd, J=4.7, 1.4 Hz, 1H), 8.83 (d, J=1.8 Hz, 1H).

Provenance & Evidence