Pyridine → ethyl 1-[(4-{3-[(Z)-2-pyridin-3-ylethenyl]-5-(trifluoromethyl)phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257392Notes

Reaction equation

HRID 1257392 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][C:9]2[CH:10]=[C:11]([C:19]3[N:20]=[C:21]([CH2:24][N:25]4[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:26]4)[S:22][CH:23]=3)[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[CH:2]=1.N1C=CC=CC=1>C(O)C.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[CH:8]\[C:9]2[CH:10]=[C:11]([C:19]3[N:20]=[C:21]([CH2:24][N:25]4[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:26]4)[S:22][CH:23]=3)[CH:12]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:14]=2)[CH:2]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 66939083ethyl 1-({4-[3-(pyridin-3-ylethynyl)-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 66939318ethyl 1-[(4-{3-[(Z)-2-pyridin-3-ylethenyl]-5-(trifluoromethyl)phenyl}-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylateYield 46.4%

Reagents, catalysts & solvents 2

HCID 17887766Palladium barium sulphateCatalystHCID 702EthanolSolvent

Procedure

To a solution (10 mL) of the compound (980 mg, 2.0 mmol) obtained in Example 87a in ethanol were added pyridine (480 mg, 6.1 mmol) and palladium-barium sulfate (490 mg), and the mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere (1 atm). Palladium-carbon was removed and the solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=35/65) to give the title compound (450 mg, 46%) as colorless crystals.

Workup

  1. customPalladium-carbon was removed
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=35/65)

Sources & evidence

ORD record
ord-0d413d4dfbc74b65a09a84867d2fa534
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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