Potassium Carbonate → HCID 89702554, compound

HRID 2203000Notes

Reaction equation

HRID 2203000 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:16])=[C:9]([CH:11]3[CH2:13][CH:12]3[C:14]#[N:15])[N:10]=2)[CH:7]=1.[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][NH:27][C:26](=[O:30])[CH:25]=2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[Cl:17][C:18]1[CH:32]=[CH:31][C:21]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][N:27]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([CH3:16])=[C:9]([CH:11]5[CH2:13][CH:12]5[C:14]#[N:15])[N:10]=4)[CH:7]=3)[C:26](=[O:30])[CH:25]=2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 89690441HCID 89690441, compound

Product 1

HCID 89702554HCID 89702554, compoundYield 43.3%

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 2-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarbonitrile (26 mg), 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (45 mg), potassium carbonate (58 mg) and dioxane (2 ml) were added CuI (7 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (5 mg), and the mixture was heated at 110° C. 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, concentrated in vacuo and purified by column chromatography (MeOH/DCM) to afford the title compound (15 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. custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-7cccec4e6a484ce69558712e5b2544bc
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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