Dimethylformamide → HCID 86651042, compound

HRID 2190737Notes

Reaction equation

HRID 2190737 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(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[F:32][C:33]([F:37])([F:36])[CH2:34][SH:35]>O>[F:32][C:33]([F:37])([F:36])[CH2:34][S:35][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

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 41339242,2,2-TrifluoroethanethiolHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 86651042HCID 86651042, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.50 g of potassium carbonate and 2 ml of DMF, 0.15 g of 2,2,2-trifluoroethanethiol was added. The reaction mixture was stirred at room temperature for 1.2 hours. Water was added to reaction mixture, which followed by extraction with ethyl acetate twice. The combined organic layers were washed with 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 0.32 g of 2-[3-(2,2,2-trifluoroethylthio)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 46”).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fb9fe85e4b44d34ab906dcab48520d6
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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