Cesium carbonate → HCID 59296174, compound

HRID 2233570Notes

Reaction equation

HRID 2233570 reaction equation
Cl[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].[F:25][C:26]1[CH:33]=[C:32]([OH:34])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].COC(C)(C)C>CN(C)C=O>[F:25][C:26]1[CH:33]=[C:32]([O:34][CH2:2][C:3]2[S:7][C:6]([C:8]3[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=3)=[N:5][C:4]=2[CH3:18])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 15413tert-Butyl methyl etherHCID 27346752-Fluoro-4-hydroxybenzonitrileHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

Product 1

HCID 59296174HCID 59296174, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

560 mg of 5-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole were dissolved in 10 ml dimethylformamide. 1.2 g of cesium carbonate and 395 mg 2-Fluoro-4-hydroxybenzonitrile was added and the mixture was stirred at room temperature for three hours. Then 50 ml of methyl-tert-butylether was added, the mixture washed with brine and dried over MgSO4. The solvent was removed in vacuo. The resulting crude material was purified by reversed phase HPLC to obtain 153 mg of 2-Fluoro-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-ylmethoxy]-benzonitrile as amorphous lyophilisate.

Workup

  1. washthe mixture washed with brine
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed in vacuo
  4. customThe resulting crude material was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-b870c47ee4d04bf3ab449390f25216e1
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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