Cesium carbonate → HCID 178521925, compound

HRID 2363701Notes

Reaction equation

HRID 2363701 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.O1CCOCC1.[NH:26]1[CH:30]=[CH:29][C:28](B(O)O)=[N:27]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:14]1([NH:13][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:30]4[CH:29]=[CH:28][NH: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

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 441359396-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2×HCID 178514837HCID 178514837, compound

Product 1

HCID 178521925HCID 178521925, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×

Procedure

300 mg of 6-iodo-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 2), 4 mL of dioxane, 4 mL of water, 185 mg of 1H-pyrazole-3-boronic acid, 45 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium and 1.077 g of caesium carbonate are placed in a microwave tube. The mixture is heated for 20 minutes in a microwave machine set at 160° C., and then cooled, diluted with 20 mL of water and extracted twice with 20 mL of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The residue is chromatographed on a silica cartridge, eluting with a gradient of dichloromethane and methanol (from 0 to 10%). The fractions containing the expected product are combined and concentrated to dryness under reduced pressure to give 40 mg of N-phenyl-6-(1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid.

Workup

  1. temperatureThe mixture is heated for 20 minutes in a microwave machine
  2. customset at 160° C.
  3. temperaturecooled
  4. extractionextracted twice with 20 mL of dichloromethane
  5. dry with materialThe combined organic phases are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue is chromatographed on a silica cartridge
  9. washeluting with a gradient of dichloromethane and methanol (from 0 to 10%)
  10. additionThe fractions containing the expected product
  11. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-62ffb68b45084f74af812ef72b3f38bc
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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