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

HRID 1174118

反応式

HRID 1174118 の反応式
[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

参加物

4

反応物 2

HCID 66144Ethyl bromopyruvateHCID 1549499Pyridine-2-carbothioamide

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7a125277526f45339d6f7ae805fcaa7b
出典データセット
uspto-grants-2010_11
特許番号
US07834043B2

関連ノート

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