Imidazole → 2-(1H-imidazol-1-yl)-6-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)-vinyl)pyridine

HRID 868970Notes

Reaction equation

HRID 868970 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH:9][C:10]2[N:11]([CH3:21])[CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)[N:3]=1.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.[Cu]I>[N:22]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH:9][C:10]3[N:11]([CH3:21])[CH:12]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[N:14]=3)[N:3]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 866878962-Bromo-6-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)vinyl)pyridine

Product 1

HCID 700971972-(1H-imidazol-1-yl)-6-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)-vinyl)pyridineYield 58%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)vinyl)pyridine (102 mg, 0.3 mmol), imidazole (41 mg, 0.6 mmol), CuI (6 mg, 0.03 mmol), and K2CO3 (124 mg, 0.9 mmol) were mixed in dimethylformamide (2 mL). The resulting solution was heated for 5 h in a microwave reactor held at a constant temperature of 160° C. The crude product was purified using reverse phase column chromatography to give 2-(1H-imidazol-1-yl)-6-(2-(1-methyl-4-phenyl-1H-imidazol-2-yl)-vinyl)pyridine (57 mg). MS (ESI): m/z 328 [M+H]+.

Workup

  1. temperatureThe resulting solution was heated for 5 h in a microwave reactor
  2. customheld at a constant temperature of 160° C
  3. customThe crude product was purified

Sources & evidence

ORD record
ord-7de6bea8937142719fafc030dd474ebf
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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