Ethyl bromopyruvate → Ethyl 2-(pyridin-4-YL)thiazole-4-carboxylate

HRID 278561Notes

Reaction equation

HRID 278561 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[N:5]1[CH:6]=[CH:7][C:2]([C:1]2[S:8][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:9]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 27237884-Pyridinecarbothioamide

Product 1

HCID 595483Ethyl 2-(pyridin-4-YL)thiazole-4-carboxylateYield 53.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of thioisonicotinamide (5.0 g) and ethyl bromopyruvate (7.22 g) in ethanol (90 ml) was heated for 5 hours under reflux and concentrated. To the residue were added sodium bicarbonate solution and ethyl acetate, and the organic layer was separated, washed with water and sodium chloride solution, dried and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate) to give pale yellow solid of ethyl 2-(4-pyridyl)-4-thiazolecarboxylate (4.55 g).

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated
  3. additionTo the residue were added sodium bicarbonate solution and ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with water and sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-940033cbb1704799b94e189e7df9d7a6
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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