Tetrahydrofuran → HCID 70979095, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(8-bromo-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile (244 mg, 0.62 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (274 mg, 1.24 mmol), tetrakis(triphenylphosphine)palladium(0) (50 mg) and potassium carbonate (350 mg, 2.53 mmol) in a mixed solution of tetrahydrofuran (10 mL) and water (1 mL) was heated at 100° C. for 30 minutes under microwave (pressure: 17.2 bar, equipment power: 150 W). The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (10 mL*3). The organic phase was separated, dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give a crude product, which was purified by column chromatography (silica gel, dichloromethane/methanol=12:1) to afford 4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile as a light yellow solid (150 mg, 59.4%). LRMS (M+H)+: calcd 407.19. found 407.

Provenance & Evidence