Dimethylformamide → 2-(4-bromo-1H-imidazol-1-yl)-3-chloropyridine

HRID 252008Notes

Reaction equation

HRID 252008 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[Cl:7][C:8]1[C:9](S(C)(=O)=O)=[N:10][CH:11]=[CH:12][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:9]2[C:8]([Cl:7])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 134334253-Chloro-2-methanesulfonylpyridineHCID 178418934HCID 178418934, compound

Product 1

HCID 668538872-(4-bromo-1H-imidazol-1-yl)-3-chloropyridineYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.0 g of 4-bromoimidazole, 1.3 g of 3-chloro-2-(methanesulfonyl)pyridine, 2.7 g of cesium carbonate and 10 ml of N,N-dimethylformamide was stirred at 100° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and water was poured into the mixture. A deposited precipitate was collected by filtration to obtain 1.7 g of 2-(4-bromo-1H-imidazol-1-yl)-3-chloropyridine of the formula:

Workup

  1. temperatureto cool to room temperature
  2. filtrationA deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-e1ef04f8f5c64eab93bd4516a8c39560
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

Loading…