Cesium carbonate → (R)-5-(6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-8-yl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-8-bromo-6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (100 mg, 0.24 mmol) in 1,4-dioxane/H2O (10:1, 2 mL) was added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one (65 mg, 0.29 mmol), Cesium carbonate (156 mg, 0.48 mmol) and Tetrakis(triphenylphosphine)palladium(0) (18.4 mg, 0.025 mmol). The mixture was purged with N2 and stirred in the microwave at 130° C. for 0.5 hr. After filtration, concentrated in vacuo and purification by prep-TLC (elute: DCM:MeOH=15:1) gave (R)-5-(6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-8-yl)pyridin-2(1H)-one (30 mg, 30%).

Provenance & Evidence