Cesium carbonate → HCID 68780102, compound

HRID 2363711Notes

Reaction equation

HRID 2363711 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[N:9]=1.[C:16]1([NH:22][C:23]([C:25]2[N:26]=[C:27]3[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][N:28]3[CH:36]=2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCOCC1.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]>[CH3:15][O:14][C:10]1[N:9]=[C:8]([C:30]2[CH:31]=[CH:32][C:27]3[N:28]([CH:36]=[C:25]([C:23]([NH:22][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[O:24])[N:26]=3)[CH:29]=2)[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 2568102-Bromo-6-methoxypyridineHCID 44136345HCID 44136345, compound

Product 1

HCID 68780102HCID 68780102, compoundYield 21.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 624 mg of caesium carbonate, 90 mg of 2-bromo-6-methoxypyridine and 17.5 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium in 10 mL of dioxane and 4 mL of water are added 160 mg of 2-phenylcarbamoylimidazo[1,2-a]pyridine-6-boronic acid. The mixture is refluxed for one hour, and then cooled and concentrated to dryness under reduced pressure. The residue is taken up in 150 mL of dichloromethane and washed with 100 mL of water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure on silica and then chromatographed on a silica cartridge, eluting with a gradient of from 0 to 35% ethyl acetate in cyclohexane. The fractions containing the pure expected product are combined and concentrated to dryness under reduced pressure to give 36 mg of 6-(6-methoxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of an off-white solid.

Workup

  1. temperatureThe mixture is refluxed for one hour
  2. temperaturecooled
  3. concentrationconcentrated to dryness under reduced pressure
  4. washwashed with 100 mL of water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure on silica
  8. customchromatographed on a silica cartridge
  9. washeluting with a gradient of from 0 to 35% ethyl acetate in cyclohexane
  10. additionThe fractions containing the pure expected product
  11. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9ed4c694a39840bd8d8006967800bbad
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

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