Potassium Carbonate → 2-bromo-4-methyl-6-(3-trifluoromethyl-1H-pyrazol-1-yl)-pyridine

HRID 1279181Notes

Reaction equation

HRID 1279181 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[N:3]=1.[F:10][C:11]([F:18])([F:17])[C:12]1[CH:16]=[CH:15][NH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([N:14]2[CH:15]=[CH:16][C:12]([C:11]([F:18])([F:17])[F:10])=[N:13]2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 112881742,6-Dibromo-4-methylpyridine

Product 1

HCID 184272852-bromo-4-methyl-6-(3-trifluoromethyl-1H-pyrazol-1-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,6-dibromo-4-methylpyridine (33 mmol, obtained according to the method disclosed by WO 94/22833), 3-trifluoromethyl-1H-pyrazole (21 mmol), potassium carbonate (45 mmol) and N,N-dimethylformamide ((50 mL) is heated at 90° C. for 4 hours. The reaction mixture is partitioned between ethyl acetate ands water. The separated organic phase is washed with brine, dried over sodium sulfate and evaporated in vacuo to provide an oily residue which is purified by flash chromatography. To yield 1.9 g of the title compound.

Workup

  1. customobtained
  2. customThe reaction mixture is partitioned between ethyl acetate ands water
  3. washThe separated organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto provide an oily residue which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-0b70f3c3691540a69001dd9e0d525ece
Source dataset
uspto-grants-2002_09
Patent number
US06448204B1

Reaction notes

Loading…