Imidazole → HCID 14581290, compound

HRID 1382193Notes

Reaction equation

HRID 1382193 reaction equation
F[C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[C:9]([C:14]([O:16][CH3:17])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=[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[C:9]([C:14]([O:16][CH3:17])=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=3)=[O:7])=[CH:4][CH:3]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 14581289HCID 14581289, compound

Product 1

HCID 14581290HCID 14581290, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of 3-(4-fluorobenzoyl)-2-carbomethoxypyridine (2.37 g, 9.14 mmol) in 30 mL of DMF is added dropwise to a solution of NaH (0.43 g, 10.75 mmol) and imidazole (0.62 g, 9.14 mmol) in 26 mL of DMF. The mixture is heated at 120° C. for 1 day, then allowed to cool, quenched with ice H2O, and extracted with EtOAc (3×50 mL). The combined organic layers are dried (Na2SO4), evaporated, and the residue chromatographed on silica gel (eluting with EtOAc-CH3OH, 9:1) to generate 3-[4-(1H-imidazol-1-yl)benzoyl]-2-carbomethoxypyridine. M.P. 150°-157° C.

Workup

  1. temperatureto cool
  2. customquenched with ice H2O
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customevaporated
  6. customthe residue chromatographed on silica gel (eluting with EtOAc-CH3OH, 9:1)

Sources & evidence

ORD record
ord-fe467fb059464282ac925c4c24888496
Source dataset
uspto-grants-1989_02
Patent number
US04806535

Reaction notes

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