Water → 2-(3-Oxo-[1,2,4]triazolo[4,3-a]pyridin-2-ylmethyl)acrylic acid methyl ester

HRID 889165ノート

反応式

HRID 889165 の反応式
[N:1]1[NH:2][C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Na+].Br[CH2:14][CH:15]([CH2:20]Br)[C:16]([O:18][CH3:19])=[O:17].O>CN(C)C=O.C(OCC)(=O)C>[CH3:19][O:18][C:16](=[O:17])[C:15]([CH2:20][N:2]1[C:3](=[O:10])[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1]1)=[CH2:14]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydride2 回HCID 814311,2,4-Triazolo(4,3-a)pyridin-3(2H)-oneHCID 140895Methyl 3-bromo-2-(bromomethyl)propanoate

生成物 1

HCID 579276032-(3-Oxo-[1,2,4]triazolo[4,3-a]pyridin-2-ylmethyl)acrylic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 2H-[1,2,4]triazolo[4,3-a]pyridin-3-one (CAS 6969-71-7) (1.0 g) in N,N-dimethylformamide (50 ml), sodium hydride (60% in oil) (355 mg) was added while stirring on ice. After stirring for 20 minutes, methyl 3-bromo-2-(bromomethyl)propionate (2.11 ml) was added dropwise. Stirring was continued for 1 hour and 30 minutes, and then sodium hydride (60% in oil) (200 mg) was added and the mixture was stirred for 3 hours. Water was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed with water and brine in that order and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography to obtain the title compound (400 mg).

後処理

  1. additionwas added
  2. stirringAfter stirring for 20 minutes
  3. stirringStirring
  4. stirringthe mixture was stirred for 3 hours
  5. washThe organic layer was washed with water and brine in that order
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by NH silica gel column chromatography

出典と根拠

ORDレコード
ord-27aa4b6cbe6a4901ad71e4490bbf1562
出典データセット
uspto-grants-2012_08
特許番号
US08252810B2

反応ノート

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