HCID 86651040, compound → HCID 66880572, compound

HRID 1913618Notes

Reaction equation

HRID 1913618 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:12]=2[N:13]=1)#[CH:2].[H][H]>[Pd].C(OCC)(=O)C>[CH2:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][C:12]=2[N:13]=1)[CH3:2]

Participants

5

Reactant 2

HCID 86651040HCID 86651040, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66880572HCID 66880572, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.34 g of 2-(3-ethynylpyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.10 g of 5% palladium on carbon and 8 ml of ethyl acetate was stirred under about one atmosphere of hydrogen at room temperature for two hours. The reaction mixture was filtered through Celite™. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.33 g of 2-(3-ethylpyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 35”).

Workup

  1. filtrationThe reaction mixture was filtered through Celite™
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4a27e5cbf0ec4bef995fed156ceb0efc
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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