Imidazole → 2-chloro-5-(1H-imidazol-1-ylmethyl)pyridine

HRID 1392912Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-chloro-5-(chloromethyl)pyridine (500 mg, 3.08 mmole) in 4 mL of dry acetonitrile is added 420 mL (6.17 mmol) of imidazole followed by 852 mg (6.17 mmol) of potassium carbonate. The reaction is heated at 80° C. for 20 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 410 mg (69% yield) of 2-Chloro-5-imidazol-1-ylmethyl-pyridine. Diagnostic C13 NMR (100 MHz, CDCl3) 47.7, 119.2, 124.9, 130.6, 131.1, 137.5, 137.8, 148.6, 151.8; MS 194.2 (M+H).

Workup

temperatureAfter cooling
customthe reaction mixture is quenched with 5 mL of water
extractionextracted three-times with methylene chloride
dry with materialdried over sodium sulfate
customConcentration of the solvent provided an oil which
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-354606aecfae4862a8371380c07ca21f
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345038B2

Reaction notes

Loading…