Imidazole → HCID 21069910, compound

HRID 1788142Notes

Reaction equation

HRID 1788142 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:13]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>O1CCCC1.CN(C)C=O>[F:21][C:19]1[CH:20]=[CH:13][C:14]([C:15]#[N:16])=[C:17]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:18]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 775452,4-Difluorobenzonitrile

Product 1

HCID 21069910HCID 21069910, compoundYield 9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of imidazole (4.45 g, 65.4 mmol) in tetrahydrofuran (30 mL) and dimethylformamide (10 mL) was added potassium carbonate (9.95 g, 72 mmol) and the mixture was stirred for 30 min at room temp. To this was added 2,4-difluorobenzonitrile (10.0 g, 72 mmol) and the mixture stirred at 90° C. for 3 h then at room temp for 2 days. The mixture was filtered and concentrated and the residue was purified by flash chromatography (SiO2) eluting with 20% to 70% ethyl acetate/hexane to give the title compound as white needles (1.1 g, 9% yield). 1H-NMR (500 MHz, CDCl3) δ ppm: 7.94 (1H, s), 7.84 (1H, dd, J=8.7, 5.6 Hz), 7.37 (1H, t, J=8.7, 5.6 Hz), 7.37 (1H, t, J=1.4 Hz), 7.29 (1H, t, J=1.1 Hz), 7.27-7.21 (2H, m). LCMS [M+H]+ calcd for C10H7N3F: 188.058; found: 188.12.

Workup

  1. stirringthe mixture stirred at 90° C. for 3 h
  2. waitat room temp for 2 days
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by flash chromatography (SiO2)
  6. washeluting with 20% to 70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-66586bd856364f78a42cba315020169c
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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