Pyrrolidine → 3-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-6-pyrrolidin-1-yl-pyridazine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (300 mg, 1.0 mmol) in toluene (5 mL) was added pyrrolidine (0.10 mL, 1.2 mmol), sodium tert-butoxide (115 mg, 1.2 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1-binaphtalene (19 mg, 0.03 mmol) and tris(dibenzylideneacetone)dipalladium chloroform complex (10 mg, 0.01 mmol). The resulting mixture was heated at 110° C. for 55 min with microwave heating. Then the reaction mixture was concentrated and extracted (ethyl acetate/brine). The organic phase was dried over sodium sulfate, concentrated and chromatographed (SiO2, dichloromethane:methanol=100:0 to 99:1) to afford the title compound as a light yellow oil (80 mg, 24%). MS: m/e=337.5 [M+H]−.

Provenance & Evidence