Triethylamine → HCID 136038172, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 7-bromoquinazolin-4(3H)-one (60 mg, 0.27 mmol, 1 equiv), 1-ethynyl-4-fluorobenzene (81 mg, 0.675 mmol, 2.5 equiv), Pd(OAc)2 (12.2 mg, 0.054 mmol, 0.2 equiv), PPh3 (63.7 mg, 0.24 mmol, 0.9 equiv), CuI (10.3 mg, 0.054 mmol, 0.2 equiv), Et3N (0.3 mL) and DMF (6 mL). A vacuum was applied and the reaction mixture was back filled with nitrogen three times. The mixture was stirred at 70° C. for 3.5 hours. After it was cooled to room temperature, the reaction mixture was diluted with H2O and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure and purified by column chromatography to give the desired product. MS (ESI): 265 (MH+); 1H NMR (300 MHz, DMSO-d6) δ 12.38-12.33 (m, 1H), 8.13 (s, 2H), 7.81 (s, 1H), 7.69-7.54 (m, 3H), 7.39-7.29 (m, 2H).

Provenance & Evidence