Ethyl bromopyruvate → ethyl 1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazole-4-carboxylate

HRID 1916884Notes

Reaction equation

HRID 1916884 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:20])[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Br[CH2:27][C:28](=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:20]=[C:9]2[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])([CH3:12])[CH3:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178449870HCID 178449870, compound

Product 1

HCID 66797364ethyl 1-(4-bromophenyl)-2-(2-(2-fluorophenyl)propan-2-yl)-1H-imidazole-4-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a 250 mL round bottom flask attached with condenser was added N-(4-bromophenyl)-2-(2-fluorophenyl)-2-methylpropanimidamide (5.0 g, 15 mmol), anhydrous THF (80 mL), NaHCO3 (2.52 g, 30 mmol), and 90% ethyl bromopyruvate (1.90 mL, 15.1 mmol). The reaction mixture was stirred at 70° C. for 2 hr prior to analysis by LCMS. The cooled reaction mixture was decanted and concentrated in vacuo. The residue was taken into toluene (65 mL) and acetic acid (1.8 mL). The solution was stirred at reflux for 1 hr. The cooled solution was washed with H2O (150 mL×3), dried over Na2SO4, filtered, concentrated in vacuo, and chromatographed through a SiO2 column using a 100% Hx to 70% EtOAc gradient to afford purified title compound (4.3 g, 67% yield). LCMS (ES): m/z=431.3, 433.3 [M+H]+.

Workup

  1. customTo a 250 mL round bottom flask attached with condenser
  2. customThe cooled reaction mixture
  3. customwas decanted
  4. concentrationconcentrated in vacuo
  5. stirringThe solution was stirred
  6. temperatureat reflux for 1 hr
  7. washThe cooled solution was washed with H2O (150 mL×3)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customchromatographed through a SiO2 column
  12. customto afford

Sources & evidence

ORD record
ord-264c1cae779945cca665dd7bd7d1dd25
Source dataset
uspto-grants-2013_12
Patent number
US08618154B2

Reaction notes

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