Water → HCID 178471916, 화합물

HRID 226927노트

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HRID 226927 반응식
Cl.[CH3:2][C:3]1[C:4]([CH3:12])=[N:5][CH:6]=[C:7]([CH:11]=1)[C:8](Cl)=[O:9].[H-].[Na+].[CH2:15]([O:17][C:18](=[O:28])[CH:19]=[CH:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:16].O>O1CCCC1>[CH2:15]([O:17][C:18](=[O:28])[C:19]([C:8]([C:7]1[CH:6]=[N:5][C:4]([CH3:12])=[C:3]([CH3:2])[CH:11]=1)=[O:9])=[CH:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 668793173-Phenylamino-acrylic acid ethyl esterHCID 866136455,6-Dimethyl-nicotinoyl chloride hydrochloride

생성물 1

HCID 178471916HCID 178471916, 화합물수율 7.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

3.31 g (16.0 mmol) of 5,6-dimethyl-nicotinoyl chloride hydrochloride 6a (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351) was dissolved in 35 mL of dry tetrahydrofuran and cooled down to −10° C. under nitrogen atmosphere. To the resultant solution was added 1.60 g (40.0 mmol) of 60% sodium hydride and the mixture was stirred for 15 minutes, followed by the addition of 3.06 g (16.0 mmol) of 3-phenylamino-acrylic acid ethyl ester 5a. The mixture was stirred at −10° C. for 2 hours, followed by the addition of 100 mL of water to the reaction mixture. The product was extracted twice with 100 mL dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated in vacuo. Purification of the crude product using flash chromatography (10-75% ethyl acetate in hexane) yielded 400 mg of 2-(5,6-dimethyl-pyridine-3-carbonyl)-3-phenylamino-acrylic acid ethyl ester 2d as a yellow solid.

후처리

  1. stirringThe mixture was stirred at −10° C. for 2 hours
  2. extractionThe product was extracted twice with 100 mL dichloromethane
  3. dry with materialThe combined organic extracts were dried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude product

출처 및 근거

ORD 기록
ord-4236e405c3b24c7e8130a89210ca8e7e
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557213B2

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