Ethyl Acetate → HCID 57803256, compound

HRID 2103400Notes

Reaction equation

HRID 2103400 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.[H-].[Na+].Cl[C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][N:14]=1.[C:23](OCC)(=O)C>CN(C=O)C>[F:20][C:19]([F:22])([F:21])[C:17]1[CH:16]=[CH:15][N:14]=[C:13]([N:1]2[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:23])=[O:7])[N:3]=[CH:2]2)[CH:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 178418785HCID 178418785, compound

Product 1

HCID 57803256HCID 57803256, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1H-imidazole-4-carboxylate (417 mg, 3.3 mmol) in DMF (10 mL) was added sodium hydride (130 mg, 3.3 mmol). After being stir for 1 h at room temperature, 2-chloro-4-(trifluoromethyl)pyridine (500 mg, 2.8 mmol) was added. The mixture was stirred at 80° C. overnight. After being cooled to room temperature, ethyl acetate was added. The solution was washed with brine several times, dried (MgSO4) and concentrated. Chromatography on silica gel eluting with EtOAc/hexanes (1:1) afforded the title compound (120 mg). MS (M+H) 272.1.

Workup

  1. stirringThe mixture was stirred at 80° C. overnight
  2. temperatureAfter being cooled to room temperature
  3. washThe solution was washed with brine several times
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d8e77d9c5475442d9f5baaf64df6e2b7
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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