Ethyl bromopyruvate → HCID 59384155, compound

HRID 1010610Notes

Reaction equation

HRID 1010610 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([C:15]([O-:17])=[O:16])[N:12]=[C:11]2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[F:25])[CH:7]=[CH:8][CH:9]=1)[CH3:2].C(OC1C=C(NC(C2C=CC(C)=CC=2F)=N)C=CC=1)C.C(=O)(O)[O-].[Na+].BrCC(=O)C(OCC)=O>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]=[C:11]2[C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=2[F:25])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 86630118HCID 86630118, compoundHCID 178466608HCID 178466608, compound

Product 1

HCID 59384155HCID 59384155, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethel 1-(3-ethoxyphenyl)-2-(2-fluoro-4-methylphenyl)-1H-imidazole-4-carboxylate. To a mixture of the compound from Step A and 0.80 g (9.5 mmol) of sodium bicarbonate in 10 mL of 1,4-dioxane was added 0.60 mL (4.8 mmol) of ethyl bromopyruvate. The reaction mixture was refluxed overnight. After cooling to room temperature, the solid was filtered off and the filtrate was concentrated in vacuo. Flash chromatography on a Biotage Horizon® system (silica gel, 0 to 50% ethyl acetate in hexanes gradient) gave the title compound as a viscous yellow oil. LC/MS 369.2 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. filtrationthe solid was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9f106efea9b64bafb914789a28a707ed
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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