Potassium Carbonate → 8-bromo-7-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

HRID 2101309

Reaction equation

HRID 2101309 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.Br[CH2:20][C:21]1[C:22]([CH3:31])=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]2[N:4]([C:15](=[O:18])[N:16]([CH2:20][C:21]3[C:22]([CH3:31])=[N:23][C:24]([C:27]([F:30])([F:28])[F:29])=[CH:25][CH:26]=3)[N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][C:11]([Cl:14])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 577994388-Bromo-7-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneHCID 598348213-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine

Product 1

HCID 577994058-bromo-7-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneYield 77.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 8-bromo-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (1.00 g, 3.08 mmol) in DMF (12 mL) at room temperature under argon was added 3-(bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine (861 mg, 3.39 mmol), followed by K2CO3 (1278 mg, 9.24 mmol). The resulting suspension was warmed to 55° C. for 8 h. After cooling the reaction mixture to room temperature, most of the solvent was removed under reduced pressure. The residue was diluted with water (˜20 mL) and shaken vigorously. A solid formed and was filtered, washed with water and air-dried. The crude product was purified by automated silica gel chromatography (eluted with EtOAc/hexanes) to obtain 1.19 g (71% yield) of title compound as a tan amorphous solid. HPLC/MS: retention time=3.90 min, [M+H]+=497.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. custommost of the solvent was removed under reduced pressure
  3. additionThe residue was diluted with water (˜20 mL)
  4. customA solid formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customair-dried
  8. customThe crude product was purified by automated silica gel chromatography (eluted with EtOAc/hexanes)

Sources & evidence

ORD record
ord-830ef4825bdf41b5a67e1ac271e90cc8
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Linked notes

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