1,10-Phenanthroline → (R)-8-bromo-1,4-dimethyl-6-(1-methyl-1H-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-8-bromo-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (292 mg, 1 mmol), 4-iodo-1-methyl-1H-pyrazole (312 mg, 1.5 mmol), copper (I) iodide (58 mg, 0.3 mmol), 1,10-phenanthroline (54 mg, 0.3 mmol) and potassium phosphate (424 mg, 2 mmol) in dimethyl sulfoxide (10 mL) was heated at 150° C. for 14 hours under nitrogen. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (20 mL×3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give (R)-8-bromo-1,4-dimethyl-6-(1-methyl-1H-pyrazol-4-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine which was used in the next step without further purification. LRMS (M+H)+: calcd 372.07. found 372.

Provenance & Evidence