Imidazole → HCID 14581299, compound

HRID 1382197Notes

Reaction equation

HRID 1382197 reaction equation
[C:1]([C:5]1[C:6]([C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=2)=[N:7][CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2].[H-].[Na+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.CCOC(C)=O.CO>CN(C=O)C>[N:22]1([C:15]2[CH:16]=[CH:17][C:12]([C:11]([C:6]3[C:5]([C:1]([O:3][CH3:4])=[O:2])=[CH:10][CH:9]=[CH:8][N:7]=3)=[O:19])=[CH:13][CH:14]=2)[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 14581298HCID 14581298, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 14581299HCID 14581299, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

A solution of 3-carbomethoxy-2-(4-fluorobenzoyl)pyridine (2.38 g, 9.18 mmol) in 7 ml of DMF is added dropwise to a mixture of NaH (0.25 g, 10.56 mmol) and imidazole (0.63 g, 9.18 mmol) in 25 mL of DMF. The mixture is heated at 120° C. for 20 hours, then allowed to cool, quenched with H2O and extracted with CH2Cl2 (4×50 mL). The combined organic layers are dried (Na2SO4) and evaporated to produce an oil. Chromatography on silica gel (using EtOAc-MeOH, 9.5:0.5 as the eluent) gives 2-[4-(1H-imidazol-1-yl)benzoyl]3-carbomethoxypyridine. M.P. 171°-173.5° C.

Workup

  1. temperatureto cool
  2. customquenched with H2O
  3. extractionextracted with CH2Cl2 (4×50 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. customevaporated
  6. customto produce an oil

Sources & evidence

ORD record
ord-e22855fdd7f048139915cfc7527805aa
Source dataset
uspto-grants-1989_02
Patent number
US04806535

Reaction notes

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