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

HRID 2280958노트

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HRID 2280958 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 2855718-Crown-6촉매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-99ade9f9c5a7450a82de0b2a2ec5be8b
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139557B2

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