Ethanol → 4-Ethoxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

A microwavable vial was charged with 4-hydroxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one (48.1 mg, 0.2 mmol), toluene (2 ml), and ethanol (23.3 μL, 0.4 mmol). Cyanomethylene-tri-n-butylphosphorane (CAS#157141-27-0, 169 mg, 0.700 mmol) was then added to the vial. The reaction vial was sealed and was heated by microwave irradiation at 105° C. for 1 hour. The reaction mixture was cooled to room temperature and diluted with dichloromethane and brine. The layers were separated and the aqueous layer was extracted an additional two times with dichloromethane. 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%). Further purification was accomplished via reverse phase HPLC (10 to 40% acetonitrile/water w/0.1% NH4OH) to afford 4-ethoxy-1-methyl-5-pyridin-3-yl-1,3-dihydro-indol-2-one; HRMS: (ESI) m/z 269.1289 (M+H)+, 1H NMR (400 MHz, CD2Cl2) δ ppm 1.16 (t, J=6.95 Hz, 3H), 3.20 (s, 3H), 3.60 (s, 2H), 3.85 (q, J=6.91 Hz, 2H), 6.68 (d, J=8.08 Hz, 1H), 7.28 (d, J=8.08 Hz, 1H), 7.32 (dd, J=7.83, 4.80 Hz, 1H), 7.85 (dt, J=7.89, 1.99 Hz, 1H), 8.51 (dd. J4.80, 1.77 Hz, 1H), 8.71 (d, J=2.78 Hz, 1H).

Provenance & Evidence