Water → Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylate

HRID 12428ノート

反応式

HRID 12428 の反応式
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:13]1([C:19]2[CH:20]=[N:21][NH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[C:13]1([C:19]2[CH:20]=[N:21][N:22]([C:2]3[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:9][CH:10]=[CH:11][N:12]=3)[CH:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1391064-PhenylpyrazoleHCID 2796614Ethyl chloronicotinate

生成物 1

HCID 66719926Ethyl 2-(4-phenyl-1H-pyrazol-1-yl)pyridine-3-carboxylate収率 79.8%

試薬・触媒・溶媒 2

HCID 2855718-Crown-6触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of 3.6 g of ethyl 2-chloronicotinate (19.4 mmol), 1.3 g of 4-phenylpyrazole (8.12 mmol), 4.4 g of K2CO3, 40 mg of 18-crown-6 and 30 mg of KI in 30 ml of N,N-dimethylformamide was stirred at 130° C. for 6 hours. For workup, H2O was added and, after extraction with ethyl acetate, the organic phase was washed with H2O and sat. NaCl solution. The crude product obtained after drying and concentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%). In total, 1.9 g of an oil were obtained, which crystallized completely on standing in a refrigerator.

後処理

  1. extractionafter extraction with ethyl acetate
  2. washthe organic phase was washed with H2O and sat. NaCl solution
  3. customThe crude product obtained
  4. customafter drying
  5. customconcentration of the solution was purified by chromatography on silica gel (eluent: CH2Cl2/methanol 1-10%)

出典と根拠

ORDレコード
ord-aeb25d55c5c44a93bfc760d7a5f85022
出典データセット
uspto-grants-2010_06
特許番号
US07728012B2

反応ノート

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