To a solution of (R)-8-bromo-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (100 mg, 0.34 mmol) in Methylbenzene (5 mL), were added 1-iodo-4-(methylsulfonyl)benzene (115.2 mg, 0.40 mmol) and 1-iodo-4-(methylsulfonyl)benzene (115.2 mg, 0.40 mmol). Cs2CO3 (222.3 mg, 0.68 mmol), tris(dibenzylideneacetone)dipalladium(0) (31.4 mg, 0.03 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (39.22 mg, 0.07 mmol) were added. The mixture was via vacuo/N2 and stirred at 90° C. for 18 h under N2 atmosphere. After concentration, the mixture was poured into water (10 mL) and extracted with dichloromethane (20 mL×3). The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and purified by prep-TLC (elute: DCM:CH3OH=10:1) to give (R)-8-bromo-1,4-dimethyl-6-(4-(methylsulfonyl)phenyl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (60 mg, 39%).
