Reaction #41261

Reaction equation

2-(4′-bromobiphenyl-4-yl)-4,5-dihydropyridazin-3(2H)-one

(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrole dihydrochloride

cesium carbonate

2-dicyclohexylphosphino-2′(N,N-dimethylamino)biphenyl

→

title compound

Yield 15.6%

2-{4′-[(3aR,6aR)-5-Methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]biphenyl-4-yl}-4,5-dihydropyridazin-3(2H)-one

Yield 15.6%

Solvents

toluene

Conditions

Workup

1. 1
   OtherA small pressure tube equipped with a magnetic stir bar
2. 2
   Otherpurging with argon the tube
3. 3
   OtherCrude product was purified by flash chromatography (silica gel, gradient 2 to 10% methanol in dichloromethane), which

Procedure

A small pressure tube equipped with a magnetic stir bar was charged with 100 mg of 2-(4′-bromobiphenyl-4-yl)-4,5-dihydropyridazin-3(2H)-one, 58 mg of (3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrole dihydrochloride, 350 mg of cesium carbonate, 15 mg of silver triflate, 4.2 mg of tris(dibenzylideneacetone)dipalladium, and 7.2 mg of 2-dicyclohexylphosphino-2′(N,N-dimethylamino)biphenyl and 2 ml of toluene. After sealing and purging with argon the tube was heated at 100° C. for 20 hours. Crude product was purified by flash chromatography (silica gel, gradient 2 to 10% methanol in dichloromethane), which yielded 17 mg of the title compound as a dark yellow oil. Mass spectroscopy gave (M+H)+ m/z 375.2, consistent with assigned structure.

Source