Cesium carbonate → HCID 59296163, compound

HRID 2233581Notes

Reaction equation

HRID 2233581 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.[CH2:14]([C:18]1[N:19]=[C:20]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)[S:21][C:22]=1[CH2:23][OH:24])[CH2:15][CH2:16][CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:14]([C:18]1[N:19]=[C:20]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][CH:26]=2)[S:21][C:22]=1[CH2:23][O:24][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 58934102HCID 58934102, compound

Product 1

HCID 59296163HCID 59296163, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg of 4-fluoro-2-trifluoromethyl benzonitrile in 5 ml of anhydrous dimethylformamide was added 200 mg of [4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol and 0.49 g of cesium carbonate. The resulting mixture was stirred at room temperature overnight, poured onto water and extracted with heptane 1/ethyl acetate 3. The organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (heptane 4/ethyl acetate 1) to give 180 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-trifluoromethyl-benzonitrile.

Workup

  1. additionpoured onto water
  2. extractionextracted with heptane 1/ethyl acetate 3
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel (heptane 4/ethyl acetate 1)

Sources & evidence

ORD record
ord-ee76d7e27d5c4462994ac7bca61426bf
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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