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

HRID 431986Notes

Reaction equation

HRID 431986 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-f2e3c0a28daf4abcb97f9210d6c1a5bc
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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