1,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene → Methyl 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-isoxazol-3-yl)indolizine-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of crude (E)-methyl 5-((hydroxyimino)methyl)indolizine-8-carboxylate (300 mg, 1.37 mmol) in THF (20 mL) was added to a stirred solution of DIB (882 mg, 2.74 mmol) and 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (750 mg, 2.74 mmol) in THF (15 mL) at rt. The mixture was heated at 68° C. for 2 h. The solvent was removed under reduced pressure and the crude product was purified by prep-TLC and then Combiflash to give methyl 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylate (70 mg, yield 10%).

Provenance & Evidence