Iodobenzene diacetate → Ethyl 8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylate

HRID 1037082Notes

Reaction equation

HRID 1037082 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.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.[Cl:48][C:49]1[CH:54]=[C:53]([C:55]([C:57]([F:60])([F:59])[F:58])=[CH2:56])[CH:52]=[C:51]([Cl:61])[CH:50]=1>C1COCC1>[Cl:48][C:49]1[CH:54]=[C:53]([C:55]2([C:57]([F:60])([F:58])[F:59])[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)[CH2:56]2)[CH:52]=[C:51]([Cl:61])[CH:50]=1

Participants

6

Reactant 4

HCID 76724Iodobenzene diacetateHCID 12217721Iodo benzene diacetateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 895779068-[(E)-(hydroxyimino)methyl]-5-indolizinecarboxylic acid ethyl ester

Product 1

HCID 86685521Ethyl 8-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylateYield 23.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of crude (E)-ethyl 8-((hydroxyimino)methyl)indolizine-5-carboxylate (0.46 mmol) in THF (5 mL) was added slowly to a stirred solution of iodobenzene diacetate, (PhI(OAc)2, DIB, 296 mg, 0.92 mmol) and 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (222 mg, 0.92 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-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-5-carboxylate (50 mg, yield 23% over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 8.66 (t, J=2.0 Hz, 1H), 7.84 (t, J=2.0 Hz, 1H), 7.68-7.71 (m, 3H), 7.25-7.27 (m, 2H), 7.06 (m, 1H), 4.43-4.56 (m, 4H), 1.41 (t, J=2.0 Hz, 3H) ppm; MS: m/z=471.7 (M+1, ESI+).

Workup

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

Sources & evidence

ORD record
ord-47b2c203441a4bc7b287717c6dadc3c5
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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