Cesium carbonate → HCID 68556217, compound

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 7-bromo-1-(4-fluorophenyl)-4-methyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (75 mg, 0.22 mmol) from step A above, bis(pinacolato)diboron (62 mg, 0.25 mmol) and potassium acetate (66 mg, 0.67 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (16 mg, 0.02 mmol) in DMF (1 mL). The mixture was refilled with nitrogen three times and then stirred at 65° C. overnight. The mixture was cooled to room temperature. Cesium carbonate (219 mg, 0.67 mmol), 3-chloro-6-trifluoromethylpyridazine (49 mg, 0.67 mmol), and water (0.5 mL) were added. The mixture was refilled with nitrogen three times and then stirred at 60° C. for 3 hours. After cooling, the mixture was partitioned between methylene chloride and water. The aqueous phase was extracted with methylene chloride (3×20 mL). The combined extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography (100:0 to 10:1 methylene chloride/methanol) to yield the desired 1-(4-fluorophenyl)-4-methyl-7-(6-(trifluoromethyl)pyridazin-3-yl)-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (71 mg, 79%) as a grey solid

Provenance & Evidence