Water → HCID 19708608, compound

HRID 725759Notes

Reaction equation

HRID 725759 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]#[N:10])[N:3]=1.[CH3:11][N:12]1[C:16]([OH:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[N:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][N:12]1[C:16]([O:17][C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]#[N:10])[N:3]=2)=[CH:15][C:14]([C:18]([F:19])([F:20])[F:21])=[N:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 197086106-Bromo-4-methyl-2-pyridinecarbonitrileHCID 178481859HCID 178481859, compound

Product 1

HCID 19708608HCID 19708608, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.6 g 2-bromo-6-cyano-4-methylpyridine, 9 g 1-methyl-3-trifluoromethyl-5-hydroxypyrazole and 9.7 g potassium carbonate were mixed in 30 ml N,N-dimethylformamide and heated to reflux for 5 hours. After cooling, the reaction mixture was poured into 300 ml water and the aqueous layer extracted three times each with 100 ml ethyl acetate. The combined extracts were dried with anhydrous magnesium sulphate and the solvent removed in vacuo. Purification by silica gel column chromatography using hexane/ethyl acetate 7:3 afforded 8.1 g (50%) of the title compound as a pale brown solid of melting point 88° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionthe aqueous layer extracted three times each with 100 ml ethyl acetate
  5. dry with materialThe combined extracts were dried with anhydrous magnesium sulphate
  6. customthe solvent removed in vacuo
  7. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-e17e0aa794fb42d38aeba9bf01cb32ad
Source dataset
uspto-grants-1998_01
Patent number
US05707932

Reaction notes

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