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

HRID 1715164노트

반응식

HRID 1715164 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

반응 조건

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-cba6c79a94254532bd647b444a6b798a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799809B2

반응 노트

불러오는 중…