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

HRID 1037089Notes

Reaction equation

HRID 1037089 reaction equation
[OH:1]/[N:2]=[CH:3]/[C:4]1[C:12]2[N:8]([CH:9]=[CH:10][CH:11]=2)[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1.[Cl:18][C:19]1[CH:24]=[C:23]([C:25]([C:27]([F:30])([F:29])[F:28])=[CH2:26])[CH:22]=[C:21]([Cl:31])[C:20]=1[Cl:32]>C1COCC1>[Cl:18][C:19]1[CH:24]=[C:23]([C:25]2([C:27]([F:30])([F:29])[F:28])[O:1][N:2]=[C:3]([C:4]3[C:12]4[N:8]([CH:9]=[CH:10][CH:11]=4)[C:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=3)[CH2:26]2)[CH:22]=[C:21]([Cl:31])[C:20]=1[Cl:32]

Participants

4

Reactant 2

HCID 498201551,2,3-Trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 895779068-[(E)-(hydroxyimino)methyl]-5-indolizinecarboxylic acid ethyl ester

Product 1

HCID 86685525Ethyl 8-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylateYield 22.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of crude (E)-ethyl 8-((hydroxyimino)methyl)indolizine-5-carboxylate (1.15 mmol) in THF (20 mL) was added slowly to a stirred solution of DIB (528 mg, 1.64 mmol) and 1,2,3-trichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (452 mg, 1.64 mmol) in THF (10 mL) at rt. The mixture was stirred for 1 h at rt. The solvent was removed under reduced pressure and the crude product was purified by prep-TLC and then Combiflash to give ethyl 8-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylate (130 mg; yield 22% over 2 steps). MS: m/z=506.7 (M+1, ESI+).

Workup

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

Sources & evidence

ORD record
ord-52384247213b449db55ec016b39f5f68
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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