Cesium carbonate → HCID 68560145, compound

Participants

Reaction Conditions

Reaction Steps

A round bottomed flask was charged with 7-bromo-4-methyl-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (0.22 g, 0.7 mmol) from step A above, bis(pinacolato)diboron (0.20 g, 0.77 mmol), potassium acetate (0.21 g, 2.1 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (57 mg, 0.07 mmol) and DMF (3.5 mL). The mixture was degassed with nitrogen (3×) and then stirred at 60° C. overnight. The mixture was cooled to room temperature, and cesium carbonate (0.68 g, 2.1 mmol), 3-chloro-6-methylpyridazine (0.14 g, 1.1 mmol) and water (1.8 mL) were added to it. The mixture was degassed with nitrogen (3×) 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 organic extract was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (methylene chloride, then 10:1 methylene chloride/methanol) to yield the desired 4-methyl-7-(6-methylpyridazin-3-yl)-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepine (0.16 g, 67%) as a grey solid.

Provenance & Evidence