Cesium carbonate → 4-(8-methoxy-1,4-dimethyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-methoxy-1,4-dimethyl-5,6-dihydro-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepine (50 mg, 0.203 mmol) in toluene (2 mL) was added 4-iodobenzonitrile (94 mg, 0.406 mmol), Bis(dibenzylideneacetone) Palladium (28 mg, 0.03 mmol), 2-dicyclohexylphosphin-2′,6′-dimethoxybiphenyl (25 mg, 0.06 mmol) and cesium carbonate (132 mg, 0.406 mmol). The mixture was purged with N2 and stirred at 110° C. for 12 hours. The reaction mixture was washed with brine (5 mL), and then the mixture was filtered. The filtrate was extracted with acetic ester (10 mL×3), the combined organic phase was dried by anhydrous sodium sulphate, and then filtered. The filtrate was concentrated and purified by preparative HPLC (Mobile phase A: water with 0.05% ammonia solution; Mobile phase B: MeCN; column temperature: 30° C., Gradient: 30-60% B 10 min) to give 4-(8-methoxy-1,4-dimethyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile (2.7 mg, 31%) as a colorless solid.

Provenance & Evidence