Water → Ethyl 1-(3-fluoro-2-pyridyl)-4-formyl-pyrazole-3-carboxylate

HRID 1517592ノート

反応式

HRID 1517592 の反応式
[CH:1]([C:3]1[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:5][NH:6][CH:7]=1)=[O:2].F[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:20][C:19]1[C:14]([N:6]2[CH:7]=[C:3]([CH:1]=[O:2])[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:5]2)=[N:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27831762,3-DifluoropyridineHCID 178470492HCID 178470492、化合物

生成物 1

HCID 58268637Ethyl 1-(3-fluoro-2-pyridyl)-4-formyl-pyrazole-3-carboxylate収率 28.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of ethyl 4-formyl-1H-pyrazole-3-carboxylate (1.6 g, 9.52 mmol), 2,3-difluorpyridine (1.20 g) and potassium carbonate (1.97 g) in dimethylformamide (8 mL) is heated and stirred at 100° C. for 1.5 h. Then, the reaction mixture is stirred at room temperature overnight. Water is added, and the organic phase is extracted with ethyl acetate, decanted, dried over magnesium sulfate and solvent evaporated under reduced pressure. Crude is purified by normal phase Isco chromatography using ethyl acetate and hexane to give 711 mg of the title compound. MS (m/z): 264 (M+1).

後処理

  1. temperatureis heated
  2. stirringThen, the reaction mixture is stirred at room temperature overnight
  3. extractionthe organic phase is extracted with ethyl acetate
  4. customdecanted
  5. dry with materialdried over magnesium sulfate and solvent
  6. customevaporated under reduced pressure
  7. customCrude is purified by normal phase Isco chromatography

出典と根拠

ORDレコード
ord-41d8fc2eb6cf4869b3e53e24b6bf0f66
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

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