Potassium Carbonate → 1-[6-(4-Methyl-1H-imidazol-1-yl)pyridin-3-yl]ethan-1-one

HRID 505575Notes

Reaction equation

HRID 505575 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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-oneHCID 178418800HCID 178418800, compound

Product 1

HCID 450967261-[6-(4-Methyl-1H-imidazol-1-yl)pyridin-3-yl]ethan-1-oneYield 67.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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

  1. temperatureThe reaction was then cooled to room temperature
  2. customThe resulting precipitate was collected on
  3. filtrationa filter
  4. washwashed generously with water
  5. customThe resulting material was dried in vacuo

Sources & evidence

ORD record
ord-a7fd66f93a10462ea08814954004a22f
Source dataset
uspto-grants-2010_08
Patent number
US07781442B2

Reaction notes

Loading…