HCID 17972196, compound → HCID 17972179, compound

HRID 460022Notes

Reaction equation

HRID 460022 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:34])/[CH:16]=[CH:17]/[C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:20][C:19]=2[CH3:33])=[CH:11][C:10]=1[CH3:35])C1C=CC=CC=1>C(O)C.O1CCOCC1.[OH-].[Pd+2].[OH-]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:34])[CH2:16][CH2:17][C:18]2[S:22][C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=3)=[N:20][C:19]=2[CH3:33])=[CH:11][C:10]=1[CH3:35]

Participants

5

Reactant 1

HCID 17972196HCID 17972196, compound2×

Product 1

HCID 17972179HCID 17972179, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2E)-1-[4-(benzyloxy)-3-methylphenyl]-3-{4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}prop-2-en-1-one (intermediate 9, 0.77 g) in ethanol (30 ml) and 1,4-dioxane (10 ml) was added to 20% palladium hydroxide (0.31 g) and hydrogenated at 21° C. for 18 hours. The reaction was filtered through Celite and the filtrate evaporated to give material which was further purified by flash column chromatography using cyclohexane:ethyl acetate (3:1) as eluent to give the title compound as a colourless oil.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. customthe filtrate evaporated
  3. customto give material which
  4. customwas further purified by flash column chromatography

Sources & evidence

ORD record
ord-c901cdc20860457583b5302cb9475b0e
Source dataset
uspto-grants-2007_03
Patent number
US07196107B2

Reaction notes

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