p-Toluenesulfonic acid → HCID 136927183, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-amino-5-bromonicotinamide (100 mg, 0.46 mmol), 3-fluorobenzaldehyde (69 mg, 0.56 mmol), NaHSO3 (40 mg, 0.38 mmol), 4-methylbenzene sulfonic acid (15 mg, 0.05 mmol) in DMAc (3 mL) was stirred at 115° C. for 1.5 h, then additional NaHSO3 (40 mg, 0.38 mmol) was added to the mixture. After 1.5 h, the third portion of NaHSO3 (40 mg, 0.38 mmol) was added to the mixture. After being stirred overnight at 115° C., the reaction mixture was concentrated in vacuo, suspended in water and filtered to give the product of 6-bromo-2-(3-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one (70 mg, yield: 47%), which was used for the next step without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 13.04 (br s, 1H), 9.07 (d, J=2.8 Hz, 1H), 8.65 (d, J=2.8 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 8.02 (dd, J=9.6, 1.6 Hz, 1H), 7.60˜7.68 (m, 1H), 7.45˜7.54 (m, 1H). MS (M+H)+: 320/322.

Provenance & Evidence