ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Hydrogen Bromide → 6-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one

HRID 70624
ノート
印刷プレビュー

反応式

HRID 70624 の反応式
[BrH:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:11]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]OCCC(C)C)=[CH:21][CH:20]=2)=[CH:12][C@@H:13]2[NH:17][C:16](=[O:18])[CH2:15][CH2:14]2)=[N:7][C:8]=1[O:9]C.C(=O)(O)[O-].[Na+].O>C(#N)C>[Br:1][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:11]([C:6]2[NH:7][C:8](=[O:9])[C:3]([Cl:2])=[CH:4][CH:5]=2)=[CH:12][C@H:13]2[CH2:14][CH2:15][C:16](=[O:18])[NH:17]2)=[CH:20][CH:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 260Hydrogen BromideHCID 962WaterHCID 516892Sodium BicarbonateHCID 67398723(5R)-5-[2-(5-chloro-6-methoxypyridin-2-yl)-2-{4-[(3-methylbutoxy)methyl]phenyl}ethenyl]pyrrolidin-2-one

生成物 1

HCID 673960336-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one収率 85%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

48% hydrobromic acid (4 mL) was added to a solution of (5R)-5-[2-(5-chloro-6-methoxypyridin-2-yl)-2-{4-[(3-methylbutoxy)methyl]phenyl}ethenyl]pyrrolidin-2-one (E:Z=1:2 mixture) (396 mg) in acetonitrile (4 mL) at room temperature, and the mixture was stirred at 70° C. for three hours. Saturated aqueous sodium bicarbonate and water were sequentially added to the reaction solution at room temperature, followed by extraction with chloroform. The organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1→5:1) to give 6-{1-[4-(bromomethyl)phenyl]-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one (E:Z=1:2 mixture) (321 mg, 85%).

後処理

  1. extractionfollowed by extraction with chloroform
  2. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=50:1→5:1)

出典と根拠

ORDレコード
ord-a28bd9dc718a485b943c6f9a802972c3
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート