1H-1,2,4-Triazole → HCID 178521927, compound

HRID 2363702Notes

Reaction equation

HRID 2363702 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[N:10]=2)[CH:7]=1.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[C:14]1([NH:13][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:24]4[N:23]=[CH:22][NH:21][N:20]=4)=[CH:7][N:6]3[CH:8]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 441359396-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2×

Product 1

HCID 178521927HCID 178521927, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

250 mg of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 2), 8 mL of N,N-dimethylformamide, 7.7 mg of palladium acetate, 197 mg of cuprous iodide and 71.3 mg of 1,2,4-triazole are placed in a microwave tube. The reaction mixture is heated for 2.5 hours in a microwave machine set at 200° C. The cooled reaction mixture is filtered, the insoluble matter is rinsed with N,N-dimethylformamide, dichloromethane and methanol and the combined filtrates are concentrated to dryness under reduced pressure. The residue is chromatographed on a silica cartridge, eluting with a 90/10 mixture of dichloromethane and methanol. The fractions containing the pure expected product are combined and evaporated to dryness under reduced pressure to give 40 mg of N-phenyl-6-(1H-1,2,4-triazol-3-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. temperatureThe reaction mixture is heated for 2.5 hours in a microwave machine
  2. customset at 200° C
  3. customThe cooled reaction mixture
  4. filtrationis filtered
  5. washthe insoluble matter is rinsed with N,N-dimethylformamide, dichloromethane and methanol
  6. concentrationthe combined filtrates are concentrated to dryness under reduced pressure
  7. customThe residue is chromatographed on a silica cartridge
  8. washeluting with a 90/10 mixture of dichloromethane and methanol
  9. additionThe fractions containing the pure expected product
  10. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-02a415c74d354b619c620d51b68f5003
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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