Imidazole → 2-(1H-Imidazol-1-yl)pyridine-4-carboxylic acid

HRID 2280185Notes

Reaction equation

HRID 2280185 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.[Cu]I>[N:11]1([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 2227012-Bromoisonicotinic acid

Product 1

HCID 269672532-(1H-Imidazol-1-yl)pyridine-4-carboxylic acidYield 108%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 2-bromoisonicotinic acid (1.87 g. 9.26 mmol), 1H-imidazole (573 mg, 8.42 mmol) and Cs2CO3 (6.03 g, 18.5 mmol) in DMSO (18.6 mL), was added CuI (176 mg, 0.926 mmol). The mixture was heated to 125° C., stirred for 18 hours, cooled to room temperature, filtered and purified by preparative HPLC (10-90% acetonitrile in water) to give the title compound as a light pink solid (1.72 g, 98%). MS 190 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. custompurified by preparative HPLC (10-90% acetonitrile in water)

Sources & evidence

ORD record
ord-1c35194b1e7249c0b189a2c72bce88d7
Source dataset
uspto-grants-2015_09
Patent number
US09138013B2

Reaction notes

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