Water → HCID 178471916、化合物

HRID 226927ノート

反応式

HRID 226927 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 178471916HCID 178471916、化合物収率 7.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4236e405c3b24c7e8130a89210ca8e7e
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

反応ノート

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