Water → HCID 49819882, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-fluoropyridine-3-boronic acid (CAS#872041-86-6, 80 mg, 0.57 mmol) in 1,2-dimethoxyethane (0.7 mL) was added water (0.3 mL) and ethanol (0.2 mL. The solution was then charged with sodium carbonate (60 mg, 0.57 mmol), 5-bromo-1-methyl-1,3-dihydro-indol-2-one (CAS#20870-90-0, 132 mg, 0.57 mmol), and dichlorobis(triphenylphosphine)palladium (II) (CAS#13965-03-2, 20.3 mg, 0.029 mmol). The reaction vessel was sealed and is heated by microwave irradiation at 150° C. for 10 minutes. The reaction mixture was cooled to room temperature, filtered and concentrated. The resulting residue was partially purified by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water vii 0.1% TEA). Final purification was accomplished via silica gel flash chromatography (methanol-dichloromethane, 0 to 7%) to afford 5-(5-fluoro-pyridin-3-yl)-1-methyl-1,3-dihydro-indol-2-one, MS: (ES+) m/z 243 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.18 (s, 3H), 3.64 (s, 2H), 7.13 (d, J=7.8 Hz, 1H), 7.73-7.77 (m, 2H), 8.03 (d, J=9.7 Hz, 1H), 8.53 (d, J=2.7 Hz, 1H), 8.79 (s, 1H).

Provenance & Evidence