2-(Tributylstannyl)pyridine → N-phenyl-6-(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxamide

HRID 2363695Notes

Reaction equation

HRID 2363695 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.C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)CCC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.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:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=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 6077842-(Tributylstannyl)pyridineHCID 441359396-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2×

Product 1

HCID 68779277N-phenyl-6-(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxamideYield 28.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

230 mg of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 2), 690 mg of 2-tributylstannylpyridine, 120 mg of tetrakis(triphenylphosphine)palladium and 4 mL of N,N-dimethylformamide are placed in a microwave tube. The reaction mixture is heated for 5 minutes in a microwave machine set at 100° C., and then for 5 minutes at 150° C. and concentrated to dryness. The residue is chromatographed on a silica cartridge, eluting with a mixture of dichloromethane and ethyl acetate. The fractions containing the expected product are combined and evaporated to dryness under reduced pressure to give 56 mg of N-phenyl-6-(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. temperatureThe reaction mixture is heated for 5 minutes in a microwave machine
  2. customset at 100° C.
  3. concentrationconcentrated to dryness
  4. customThe residue is chromatographed on a silica cartridge
  5. washeluting with a mixture of dichloromethane and ethyl acetate
  6. additionThe fractions containing the expected product
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7fc88acf6f34434e94d9838e3ec4d6bd
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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