Potassium Carbonate → 1-(6-(4-Methyl-1H-imidazol-1-yl)pyridin-3-yl)ethanone

HRID 1643248Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([C:2]2[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH:16]=1

Participants

Conditions

Temperature: 110 °C

Procedure

1-(6-chloro-pyridin-3-yl)-ethanone (7.00 g, 45.16 mmol) and 4-methylimidazole (11.11 g, 135.50 mmol) were combined in DMSO (35 ml), before addition of K2CO3. The mixture was heated at 110° C. for 22 h with rapid stirring. The reaction was then cooled to room temperature and poured into ice water (400 ml) with vigorous stirring for 15 min. The resulting precipitate was collected on a filter and washed generously with water. The resulting material was dried in vacuo to yield 19 as a tan solid (6.1 g, 67%). LC/MS: [M+1]+=202.2. C11H11N3O=201.2. 1H NMR (DMSO-d6) 300 MHz δ2.18 (3H, s), 2.63 (3H, s), 7.72 (1H, s), 7.87 (2H, d, J=9.0 Hz), 8.41 (2H, d, J=9.0 Hz), 8.51 (1H, s), 8.98 (1H, s).

Workup

temperatureThe reaction was then cooled to room temperature
customThe resulting precipitate was collected on
filtrationa filter
washwashed generously with water
customThe resulting material was dried in vacuo

Sources & evidence

ORD record: ord-4edb05fc0e2849d89f216b57cfe971e1
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119680B2

Reaction notes

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