Ethyl bromopyruvate → Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate

HRID 1174118Notes

Reaction equation

HRID 1174118 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[S:9])[NH2:8].Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[S:9][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:8]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 1549499Pyridine-2-carbothioamide

Product 1

HCID 10082761Ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylateYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of the product of Example 3H (25.4 mmol) in ethanol (50 mL) was treated with ethyl bromopyruvate (3 mL, 23.9 mmol) and molecular sieves (10 g, 3 Å), heated at reflux for 16 hours, cooled to 25° C., filtered and concentrated. The concentrate was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane to give the title compound (1.98 g, 33% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was partitioned between ethyl acetate and saturated NaHCO3
  6. washthe organic phase was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel eluting with 0-25% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-7a125277526f45339d6f7ae805fcaa7b
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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