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

N-methyl-2-pyrrolidone → 5-Cyano-3,4-difluoro-2-(2-fluorophenylamino)-benzoic acid methyl ester

HRID 500576
ノート
印刷プレビュー

反応式

HRID 500576 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8](Br)[C:7]([F:11])=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20].[CH3:22][N:23]1C(=O)CCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].[C-]#N.[C-]#N.[Zn+2]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:22]#[N:23])[C:7]([F:11])=[C:6]([F:12])[C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20]
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 2

HCID 13387N-methyl-2-pyrrolidoneHCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

生成物 1

HCID 865986425-Cyano-3,4-difluoro-2-(2-fluorophenylamino)-benzoic acid methyl ester

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒

反応条件

温度
120 °C

実験手順

A mixture of 5-bromo-3,4-difluoro-2-(2-fluorophenylamino)-benzoic acid methyl ester (1.00 equiv.), dppf (0.02 equiv.), Pd2dba3 (0.01 equiv.), and Zn(CN)2 (0.60 equiv.) in NMP is stirred at 120° C. in a sealed tube. After stirring for 20 hours, the reaction mixture is cooled to room temperature and quenched with a 4:1:4 (volume) mixture solution of saturated aqueous NH4Cl-conc NH4O-water. The mixture is extracted with EtOAc. The organic layer is washed with saturated aqueous NH4Cl/concentrated NH4OH/water, and brine. The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that is purified by flash column chromatography to afford the desired product.

後処理

  1. stirringAfter stirring for 20 hours
  2. temperaturethe reaction mixture is cooled to room temperature
  3. customquenched with a 4:1:4 (volume) mixture solution of saturated aqueous NH4Cl-conc NH4O-water
  4. extractionThe mixture is extracted with EtOAc
  5. washThe organic layer is washed with saturated aqueous NH4Cl/concentrated NH4OH/water, and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give the crude material that
  10. customis purified by flash column chromatography

出典と根拠

ORDレコード
ord-a7036860263343c48869817e57257f9a
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07772234B2

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