Potassium Carbonate → HCID 57799411, compound

HRID 2101286Notes

Reaction equation

HRID 2101286 reaction equation
[Br:1][C:2]1[C:3]2[N:4]([C:9](=[O:12])[NH:10][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[CH2:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]2[N:4]([C:9](=[O:12])[N:10]([CH2:14][C:15]3[C:16]([CH3:25])=[N:17][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:19][CH:20]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 577994478-bromo-7-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneHCID 598348153-(Chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine

Product 1

HCID 57799411HCID 57799411, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-bromo-7-chloro-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (456 mg, 2.0 mmol) in anhydrous DMF (7 mL) was added 3-(chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine (627 mg, 3.0 mmol), followed by anhydrous potassium carbonate (415 mg, 3.0 mmol). The resulting suspension was stirred under argon at 80° C. for 1.5 h. After cooling to room temperature, the reaction mixture was partitioned between EtOAc and water, and the aqueous layer was extracted with EtOAc (30 mL×2). The combined EtOAc extracts were washed with water, then saturated aqueous NaCl, dried over Na2SO4, and evaporated under reduced pressure to provide crude product as a brown solid. The crude product was purified using a silica gel cartridge (40 g) eluted with a gradient of EtOAc (0-60%) in hexanes to afford the title compound as an off-white solid (733 mg, 87%). HPLC/MS: retention time=3.36 min, [M+H]+=420.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. extractionthe aqueous layer was extracted with EtOAc (30 mL×2)
  4. washThe combined EtOAc extracts were washed with water
  5. dry with materialsaturated aqueous NaCl, dried over Na2SO4
  6. customevaporated under reduced pressure
  7. customto provide crude product as a brown solid
  8. customThe crude product was purified
  9. washeluted with a gradient of EtOAc (0-60%) in hexanes

Sources & evidence

ORD record
ord-cd6a2c6904fc465e966c7af66643f26c
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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