Ethyl bromopyruvate → Ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(4-fluorophenyl)-1H-imidazole-4-carboxylate

HRID 1010613Notes

Reaction equation

HRID 1010613 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[NH:13])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].Br[CH2:27][C:28](=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30]>O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:13]=[C:12]3[C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178511896HCID 178511896, compound

Product 1

HCID 67297295Ethyl 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(4-fluorophenyl)-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of the compound from Step A and 4.0 g (48 mmol) of sodium bicarbonate in 50 mL of 1,4-dioxane was added 3.0 mL (24 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 yellow solid. LC/MS 369.1 (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-d513139fe80c4988b20c515d62146156
Source dataset
uspto-grants-2011_07
Patent number
US07977339B2

Reaction notes

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