Water → ethyl 1-[(4-bromo-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

HRID 1257341ノート

反応式

HRID 1257341 の反応式
[Br:1][C:2]1[N:3]=[C:4]([CH2:7]Cl)[S:5][CH:6]=1.[NH:9]1[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:10]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([CH2:7][N:9]2[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:11]=[N:10]2)[S:5][CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 581279614-Bromo-2-(chloromethyl)-1,3-thiazole

生成物 1

HCID 58127892ethyl 1-[(4-bromo-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution (4 mL) of the compound (1.57 g, 7.39 mmol) obtained in Example 30b in N,N-dimethylformamide were added ethyl 1H-pyrazole-4-carboxylate (1.3 g, 9.28 mmol) and potassium carbonate (1.5 g, 10.9 mmol), and the mixture was stirred at 80° C. overnight. The reaction mixture was allowed to cool to room temperature, water was added and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (1.51 g, 66%) as a pale-brown oil.

後処理

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

出典と根拠

ORDレコード
ord-8fb6c95600394397a71530674883142d
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

反応ノート

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