1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene → HCID 86685516, compound

Participants

Reaction Conditions

Reaction Steps

A solution of crude (E)-methyl 5-((hydroxyimino)methyl)indolizine-8-carboxylate (1.0 mmol) in THF (10 mL) was added to a stirred solution of DIB (644 mg, 2.0 mmol) and 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (480 mg, 2.0 mmol) in THF (15 mL) at rt. Then 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 Combiflash to give methyl 5-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylate (30 mg; yield 7% over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 8.52 (d, J=2.0 Hz, 1H), 7.77 (t, J=1.6 Hz, 1H), 7.57-7.62 (m, 3H), 7.23-7.27 (m, 2H), 7.06 (m, 1H), 4.57 (d, J=18.0 Hz, 1H), 4.46 (d, J=18.0 Hz, 1H), 3.87 (s, 3H) ppm; MS: m/z=456.7 (M+1, ESI+).

Provenance & Evidence