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

HRID 1037069Notes

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])[CH:19]=1>C1COCC1>[Cl:17][C:18]1[CH:23]=[C:22]([C:24]2([C:26]([F:29])([F:27])[F:28])[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])[CH:19]=1

Participants

Conditions

Temperature: 68 °C

Procedure

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+).

Workup

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

Sources & evidence

ORD record: ord-bec4dbf9f8a74527bc861c3a876d5bd4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546357B2

Reaction notes

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