Pyrrole-2-carboxaldehyde → HCID 71815317, compound

Participants

Reaction Steps

1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (75 mg, 0.32 mmol) was chlorinated by thionyl chloride (0.1 mL, 1.38 mmol) in the presence of DMF in dichloromethane (10 mL). Reaction mixture was healed to reflux for 2 h. Solvent and excess thionyl chloride was removed in vacuo. Resultant residue was made to react to 5-aminooxindole (50 mg, 0.41 mmol) in the presence of TEA (0.2 mL, 1.43 mmol) in DMF (5 mL) under RT for 1 h. Crude product extracted by ethyl acetate (EA), washed with brine (50 mL). Residue after solvent removal was made to react with pyrrole-2-carboxaldehyde (32 mg, 0.37 mmol) in the presence of catalytic pyrrolidine in ethanol under reflux for 10 h. The solid product was collected by suction filtration, washed with ethanol. Prolonged drying in vacuo yielded the title compound D104: YD: 30% (over 3 steps); mp>300° C. 1H-NMR (400 MHz, DMSO-d6): 13.30 (s, 1H), 11.92 (s, 1H), 10.84 (s, 1H), 8.56 (dd, J=7.2, 2 Hz, 1H), 8.07 (dd, J=6.6, 2 Hz, 1H), 7.92 (d, J=1.6 Hz, 1H), 7.76 (s, 1H), 7.61-7.54 (m, 3H), 7.43 (d, J=8.4, 1.6 Hz, 2H), 7.34 (s, 1H), 6.85-6.83 (m, 2H), 6.71 (dd, J=7.2, 6.8 Hz, 1H), 6.34 (s, 1H). MS (ESI): 439 (M−H)−. (C25H17FN4O3) C, H, N.

Provenance & Evidence