Dimethylformamide → 1-(3-Cyanophenyl)-4-(5-fluoro-2-pyridyl)-1H-imidazole

HRID 2216878Notes

Reaction equation

HRID 2216878 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[N:6][CH:7]=1.F[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(Cl)(Cl)Cl>[C:17]([C:16]1[CH:15]=[C:14]([N:11]2[CH:12]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=3)[N:9]=[CH:10]2)[CH:21]=[CH:20][CH:19]=1)#[N:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 678803-FluorobenzonitrileHCID 178505535HCID 178505535, compound

Product 1

HCID 219424621-(3-Cyanophenyl)-4-(5-fluoro-2-pyridyl)-1H-imidazoleYield 56.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a screw-cap vial, added 4-(5-Fluoro-2-pyridyl)imidazole (0.06 g, 0.30 mmol), 3-Fluorobenzonitrile (0.04 ml, 0.36 mmol), potassium carbonate (0.21 g, 1.5 mmol) and dimethylformamide (1 ml). Stirred the resulting reaction mixture at 110° C. overnight. Cooled the reaction mixture to room temperature, diluted with chloroform (50 ml), sequentially washed with water, (50 ml) and brine (50 ml). The organic phase was dried (sodium sulfate), filtered and concentrated in-vacuo. The crude residue was triturated with 10% diethyl ether in hexanes to yield the title compound (45 mg) as a dirty yellow colored solid. 1H—NMR (CDCl3), δ (ppm): 8.43 (d, 1H), 8.04 (dd, 1H), 7.93 (dd, 2H), 7.70 (m, 4H), 7.48 (dt, 1H).

Workup

  1. customthe resulting reaction mixture at 110° C. overnight
  2. washsequentially washed with water, (50 ml) and brine (50 ml)
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo
  6. customThe crude residue was triturated with 10% diethyl ether in hexanes

Sources & evidence

ORD record
ord-2d9c539350d6452cb52aecbb748c11b2
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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