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

HRID 1037085Notes

Reaction equation

[OH:1]/[N:2]=[CH:3]/[C:4]1[N:5]2[C:9]([C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:12]=1)=[CH:8][CH:7]=[CH:6]2.[Cl:17][C:18]1[CH:23]=[C:22]([C:24]([C:26]([F:29])([F:28])[F:27])=[CH2:25])[CH:21]=[C:20]([Cl:30])[C:19]=1[Cl:31]>C1COCC1>[Cl:17][C:18]1[CH:23]=[C:22]([C:24]2([C:26]([F:29])([F:28])[F:27])[O:1][N:2]=[C:3]([C:4]3[N:5]4[C:9]([C:10]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:12]=3)=[CH:8][CH:7]=[CH:6]4)[CH2:25]2)[CH:21]=[C:20]([Cl:30])[C:19]=1[Cl:31]

Participants

Conditions

Temperature: 68 °C

Procedure

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%).

Workup

customThe solvent was removed under reduced pressure
customthe crude product was purified by prep-TLC and then Combiflash

Sources & evidence

ORD record: ord-7444d73fb1a4496da04ce1a1fdad3440
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546357B2

Reaction notes

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