Ethyl bromopyruvate → HCID 68780924, compound

HRID 2363712Notes

Reaction equation

HRID 2363712 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[CH3:8].Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(COC)OC>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:11]([C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][N:6]=3)=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=2)[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 9596135-Iodo-6-methylpyridin-2-amine

Product 1

HCID 68780924HCID 68780924, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 2 g of 5-iodo-6-methylpyridine-2-amine in 15 mL of dimethoxyethane are added 1.3 mL of ethyl bromopyruvate. The reaction mixture is stirred at 20° C. for 16 hours and then concentrated to dryness, taken up in 15 mL of ethanol, refluxed for 2.5 hours and finally concentrated under reduced pressure. The residue is taken up in a mixture of dichloromethane and saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and concentrated to dryness under reduced pressure to give 2.77 g of ethyl 6-iodo-5-methyl(pyrid-2-yl)imidazo[1,2-a]pyridine-2-carboxylate in the form of a beige-coloured solid.

Workup

  1. concentrationconcentrated to dryness
  2. temperaturerefluxed for 2.5 hours
  3. concentrationfinally concentrated under reduced pressure
  4. additionThe residue is taken up in a mixture of dichloromethane and saturated sodium bicarbonate solution
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-ace58320a9594ae8a6188a4f94215da4
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

Loading…