Potassium Carbonate → HCID 52919792, compound

HRID 2190730Notes

Reaction equation

HRID 2190730 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.[C:21](=O)([O-])[O-:22].[K+].[K+]>CO>[CH3:21][O:22][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 52919792HCID 52919792, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.27 g of potassium carbonate and 3 ml of methanol was stirred while heating at 60° C. for two hours. The reaction mixture was concentrated under reduced pressure. Water was added thereto, which followed by extraction with ethyl acetate twice. The combined organic layers were washed with water and a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.21 g of 2-(3-methoxypyridin-4-yl)-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 37”).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added
  3. extractionwhich followed by extraction with ethyl acetate twice
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83789775d28c4af9bb2659963762fb88
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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