Dimethylformamide → HCID 66788350, compound

Participants

Reaction Conditions

Reaction Steps

To 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one, prepared as described in Example 3a (124 mg, 0.45 mmol) was added bromo-pyridine-3-sulfonic acid 4-fluoro-benzylamide (140 mg, 0.41 mmol), tripotassium phosphate (260 mg, 1.25 mmol) and DMF (2.5 mL). The reaction mixture was degassed and placed under an argon atmosphere, at which time tetrakis(triphenylphosphine)palladium(0), (23 mg, 0.02 mmol)] was added. The reaction vessel was sealed and was heated by microwave irradiation at 100° C. for 60 minutes. The reaction mixture was then 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 (heptane-ethyl acetate, 20 to 100%) to furnish 5-(1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-pyridine-3-sulfonic acid 4-fluoro-benzylamide; HRMS: (ESI) m/z 412.1136 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.17 (s, 3H), 3.65 (s, 2H), 4.12 (s, 2H), 7.03 (t, J=8.8 Hz, 2H), 7.14 (d, J=8.1 Hz, 1H), 7.25 (dd, J=8.6, 5.6 Hz, 2H), 7.65 (s, 1H), 7.67 (d, J=8.1 Hz, 1H), 8.20 (t, J=2.3 Hz, 1H), 8.44 (t, J=6.3 Hz, 1H), 8.80 (d, J=2.0 Hz, 1H), 9.04 (d, J=2.3 Hz, 1H).

Provenance & Evidence