Sodium Carbonate → 6-Chloro-3-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine

HRID 383310Notes

Reaction equation

HRID 383310 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[C:18](B(O)O)[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:18]3[CH:17]=[CH:16][N:15]=[C:14]([O:13][CH3:12])[CH:19]=3)=[CH:3][N:4]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 23546919(2-Methoxypyridin-4-yl)boronic acidHCID 457900423-Bromo-6-chloroimidazo[1,2-a]pyridine

Product 1

HCID 684860916-Chloro-3-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-bromo-6-chloro-imidazo[1,2-a]pyridine (1 eq, 0.72 mmol, 0.2 g), 2-methoxypyrid-4-yl boronic acid (1.0 eq, 0.72 mmol, 0.11 g), Na2CO3 (2 eq, 1.44 mmol, 0.152 g) in dioxane (0.6 ml) and water (0.2 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (50 mg). The reaction mixture is heated using microwave radiation at 100° C. for 2 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-25% EtOAc in iso-hexane to afford the title compound; [M+H]+=260 (262).

Workup

  1. temperatureThe reaction mixture is heated
  2. customat 100° C.
  3. customfor 2 hours
  4. extractionextracted with EtOAc
  5. washThe combined organic portions are washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography on silica eluting with 0-25% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-82c5cfae7b994e2eb3b770a3f16b4eb8
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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