Dimethylformamide → 2-[3-(2,2,2-Trifluoroethyl)oxypyridin-4-yl]-5-(trifluoromethyl)benzoxazole

HRID 2094373Notes

Reaction equation

HRID 2094373 reaction equation
[H-].[Na+].CN(C=O)C.[F:8][C:9]([F:13])([F:12])[CH2:10][OH:11].F[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:24]=2[N:25]=1>O>[F:8][C:9]([F:13])([F:12])[CH2:10][O:11][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[C:21]1[O:22][C:23]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:24]=2[N:25]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 866510412-[3-(2,2,2-Trifluoroethyl)oxypyridin-4-yl]-5-(trifluoromethyl)benzoxazoleYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.06 g of 55% sodium hydride (in oil) and 2 ml of DMF was stirred at room temperature. To the mixture, a mixture solution of 0.13 g of 2,2,2-trifluoroethanol and 0.5 ml of DMF was added. The mixture solution was stirred at the same temperature for 15 minutes, and then 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole was stirred at room temperature for one hour. Water was added to the reaction mixture, which followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.27 g of 2-[3-(2,2,2-trifluoroethyl)oxypyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 39”).

Workup

  1. stirringThe mixture solution was stirred at the same temperature for 15 minutes
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4365ee74e0841379bdbd5cb951a514d
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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