Water → HCID 59556340, compound

HRID 1172686Notes

Reaction equation

HRID 1172686 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]([C:5]1[S:9][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:7][C:6]=1[CH3:20])[OH:4].Br[CH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([F:33])[CH:26]=1.[H-].[Na+].O>CN(C)C=O>[F:33][C:27]1[CH:26]=[C:25]([CH2:24][O:4][CH:3]([C:5]2[S:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=3)=[N:7][C:6]=2[CH3:20])[C:2]([F:1])([F:21])[F:22])[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27784664-Cyano-3-fluorobenzyl bromideHCID 59556354HCID 59556354, compound

Product 1

HCID 59556340HCID 59556340, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.30 g 2,2,2-Trifluoro-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol and 815 mg 4-Bromomethyl-2-fluoro-benzonitrile were dissolved in 40 ml dimethylformamide. 192 mg sodium hydride were added and the mixture stirred at room temperature for one hour. Then 15 ml water were added and the mixture extracted three times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent removed in vacuo. The residue was purified by reversed phase HPLC to obtain 840 mg 2-Fluoro-4-{2,2,2-trifluoro-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxymethyl}-benzonitrile as an oil.

Workup

  1. extractionthe mixture extracted three times with portions of 50 ml ethyl acetate
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-88592dff3f3f4788ab9a4bdcf24fbf71
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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