Potassium Carbonate → HCID 121386212, compound

HRID 2202996Notes

Reaction equation

HRID 2202996 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:19])=[C:9]([CH:11]3[CH2:13][CH:12]3[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=2)[CH:7]=1.[Cl:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][NH:30][C:29](=[O:33])[CH:28]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O1CCOCC1>[Cl:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][N:30]([C:2]3[CH:3]=[CH:4][C:5]4[N:6]([C:8]([CH3:19])=[C:9]([CH:11]5[CH2:13][CH:12]5[C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=4)[CH:7]=3)[C:29](=[O:33])[CH:28]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 121386225Ethyl 2-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxylate

Product 1

HCID 121386212HCID 121386212, compoundYield 88.1%

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 ethyl 2-(6-iodo-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxylate (280 mg), 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (140 mg), potassium carbonate (243 mg) and dioxane (2 ml) were added CuI (57 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (43 mg), and the mixture was heated at 110° C. for 12 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The resulting 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 (250 mg) as a white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe resulting 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-474eb6c644ee4f9fb56387bc38c77414
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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