2,6-difluoro-N-(4-(prop-1-en-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide → 2,6-Difluoro-N-(4-isopropyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamide

HRID 1255132Notes

Reaction equation

HRID 1255132 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[C:10]([C:12]([CH3:14])=[CH2:13])[N:11]=1)=[O:5].[H][H]>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[C:4]([NH:6][C:7]1[S:8][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)=[C:10]([CH:12]([CH3:13])[CH3:14])[N:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 247655792,6-difluoro-N-(4-(prop-1-en-2-yl)-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 590045452,6-Difluoro-N-(4-isopropyl-5-(3-(trifluoromethyl)phenyl)thiazol-2-yl)benzamideYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Into a solution of Compound 68a (63.6 mg, 0.15 mmol) in EtOAc (2.0 mL) was added 5% Pd/C (50 mg). The mixture was stirred at room temperature under 1 atmosphere of hydrogen for 2 hours. The mixture was filtered through a short plug of silica, the filtrate was concentrated, the residue was purified by column chromatography on silica gel (eluted with 10-70% ethyl acetate in hexanes) to give Compound 69 (46 mg, 72%) as a white solid.

Workup

  1. filtrationThe mixture was filtered through a short plug of silica
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by column chromatography on silica gel (eluted with 10-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7129927586ea44b0ada59a265f48a30a
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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