Potassium Carbonate → HCID 89690619, compound

HRID 2202980Notes

Reaction equation

HRID 2202980 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:7]=1.[F:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[CH3:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([N:23]3[CH:24]=[CH:25][C:20]([O:19][CH2:18][C:17]4[CH:27]=[CH:28][C:14]([F:13])=[CH:15][CH:16]=4)=[CH:21][C:22]3=[O:26])=[CH:7][N:6]2[C:8]=1[CH3:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-oneHCID 70251217HCID 70251217, compound

Product 1

HCID 89690619HCID 89690619, compoundYield 30.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 6-iodo-2,3-dimethylimidazo[1,2-a]pyridine (204 mg), 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (150 mg), potassium carbonate (283 mg) and dioxane (15 ml) were added CuI (51 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (38 mg), and the mixture was heated at 110° C. in a sealed tube for 16 h. The reaction mixture was then cooled to room temperature, and concentrated in vacuo. The residue was diluted with DCM, washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography (MeOH/DCM) to afford the title compound (75 mg) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-91d9d94eaead4dc4922e7f2b4d39f089
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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