Triethylamine → HCID 67508261, compound

HRID 623443Notes

Reaction equation

HRID 623443 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[CH:6][C:5]([F:11])=[C:4]([O:12][CH2:13][C:14]([F:17])([F:16])[F:15])[N:3]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[F:11][C:5]1[CH:6]=[C:7]([C:8](=[O:10])[CH3:9])[CH:2]=[N:3][C:4]=1[O:12][CH2:13][C:14]([F:15])([F:16])[F:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 87426965HCID 87426965, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67508261HCID 67508261, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(2-chloro-5-fluoro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanone (0.23 g, 0.86 mmol, Step-3) and triethylamine (0.17 mL, 1.20 mmol) in ethanol (9 mL) is stirred at room temperature for 1 hour. Then 10% palladium on carbon (0.03 g, 0.28 mmol) is added to the mixture. The mixture is stirred at room temperature under a balloon of hydrogen gas for 5 hours. After filtration through a pad of celite, the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (5:1) to give 0.15 g (76% yield) of the title compound as colorless oil.

Workup

  1. filtrationAfter filtration through a pad of celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-d63232317cf943ba8ef5d85303a9ffc7
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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