2-Bromopyridine → 4-(3-cyanophenyl)-1-(2-pyridyl)-1H-imidazole

HRID 2216889Notes

Reaction equation

HRID 2216889 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1>CN1CCCC1=O.ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[CH:11][N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 79732-BromopyridineHCID 178509695HCID 178509695, compound

Product 1

HCID 98781404-(3-cyanophenyl)-1-(2-pyridyl)-1H-imidazoleYield 9.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A solution of 4-(3-cyanophenyl)imidazole (0.02 g, 0.11 mmol) in N-methylpyrrolidinone (0.5 mL) was treated with 2-bromopyridine (1.05 mL, 11.1 mmol) and the reaction mixture heated overnight at 160° C. After cooling the reaction mixture was diluted with dichloromethane (40 mL) and the organic phase was successively washed with water (10×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography using 30% ethyl acetate in hexanes afforded 2.5 mg (9%) of 4-(3-cyanophenyl)-1-(2-pyridyl)-1H-imidazole, as an off-white solid.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washthe organic phase was successively washed with water (10×50 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e7532b7a4974c48ad7e80b2fd652998
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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