Ethyl [2-methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethenyl)phenoxy]acetate → HCID 16109179, compound

HRID 460035Notes

Reaction equation

HRID 460035 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH:15]=[CH:16][C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]>[Pd].C(O)C.O1CCOCC1>[CH3:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)=[N:19][C:18]=2[CH3:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 1

HCID 86592488Ethyl [2-methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethenyl)phenoxy]acetate2×

Product 1

HCID 16109179HCID 16109179, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

A mixture of ethyl [2-methyl-4-(2-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethenyl)phenoxy]acetate (intermediate 19, 0.23 g) and 10% palladium on carbon (0.2 g) in ethanol:1,4-dioxan (1:1, 20 ml) was stirred under a hydrogen atmosphere for 6 hours. The reaction mixture was filtered through Celite™ and the filtrate evaporated. The residue was purified by Biotage™ chromatography using a mixture of petroleum ether:ethyl acetate (4:1) as eluent to give the title compound as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. customthe filtrate evaporated
  3. customThe residue was purified by Biotage™ chromatography
  4. additiona mixture of petroleum ether:ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-0631962fb67b4dbdac10f3e7f1dc8f7f
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

Loading…