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

HRID 1174118

반응식

HRID 1174118 반응식
[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

참가 물질

4

반응물 2

HCID 66144Ethyl bromopyruvateHCID 1549499Pyridine-2-carbothioamide

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7a125277526f45339d6f7ae805fcaa7b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834043B2

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