Potassium Carbonate → HCID 121386239, compound

HRID 2202989Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine (1.9 g), methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (1.0 g), potassium carbonate (901 mg) and dioxane (30 ml) were added CuI (248 mg) and trans-N,N′-dimethyl-cyclohexane-1,2-diamine (308 mg), and the mixture was heated at 110° C. in a sealed tube for 16 h. The reaction mixture was cooled to room temperature, concentrated in vacuo, and diluted with a mixture of DCM and MeOH. The insoluble material was removed by filtration, and the filtrate was concentrated in vacuo and purified by column chromatography (MeOH/DCM) to afford the title compound (550 mg) as a brown solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated in vacuo
additiondiluted with a mixture of DCM and MeOH
customThe insoluble material was removed by filtration
concentrationthe filtrate was concentrated in vacuo
custompurified by column chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-1d935ab6cc524111a9ed19f3663b04ce
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365540B2

Reaction notes

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