Imidazole → HCID 14581300, compound

HRID 1382201Notes

Reaction equation

HRID 1382201 reaction equation
F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][C:13]=2[C:14]([O:16][CH3:17])=[O:15])=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>CN(C=O)C>[N:22]1([C:2]2[CH:19]=[CH:18][C:5]([C:6]([C:8]3[CH:9]=[N:10][CH:11]=[CH:12][C:13]=3[C:14]([O:16][CH3:17])=[O:15])=[O:7])=[CH:4][CH:3]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 21274427HCID 21274427, compound

Product 1

HCID 14581300HCID 14581300, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of 3-(4-fluorobenzoyl)-4-carbomethoxypyridine (2.25 g, 8.68 mmol) in 10 mL of DMF is added dropwise to a solution of NaH (0.25 g, 10.21 mmol) and imidazole (0.59 g, 8.68 mmol) in 26 mL of DMF. The mixture, after heating at 120° C. for 1 day, is allowed to cool, quenched with ice water, and extracted with EtOAc (3×75 mL). The combined organic layers are dried (Na2SO4) and evaporated to produce crude product. Chromatographic purification on silica gel (using EtOAc-MeOH, 9:1 as the eluent) gives pure 3-[4-(1H-imidazol-1-yl)benzoyl]-4-carbomethoxypyridine as a light brown solid. M.P. 125°-128° C.

Workup

  1. temperatureto cool
  2. customquenched with ice water
  3. extractionextracted with EtOAc (3×75 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customevaporated
  6. customto produce crude product
  7. customChromatographic purification on silica gel (

Sources & evidence

ORD record
ord-2830e4da59594a298e778ead0fdeb89e
Source dataset
uspto-grants-1989_02
Patent number
US04806535

Reaction notes

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