Pentafluorophenol → 2-(perfluorophenoxy)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 40843

反応式

HRID 40843 の反応式
CS[C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:16]=3)[N:11]([S:22]([C:25]3[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:10]=2)[C:6]([C:32]#[N:33])=[CH:5][N:4]=1.ClC1C=CC=C(C(OO)=O)C=1.[F:45][C:46]1[C:51]([OH:52])=[C:50]([F:53])[C:49]([F:54])=[C:48]([F:55])[C:47]=1[F:56]>ClCCl>[F:45][C:46]1[C:47]([F:56])=[C:48]([F:55])[C:49]([F:54])=[C:50]([F:53])[C:51]=1[O:52][C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]([F:19])([F:20])[F:21])[CH:16]=3)[N:11]([S:22]([C:25]3[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=3)(=[O:24])=[O:23])[CH:10]=2)[C:6]([C:32]#[N:33])=[CH:5][N:4]=1

参加物

5

反応物 3

HCID 13041PentafluorophenolHCID 70297m-Chloroperbenzoic acidHCID 594145372-(Methylthio)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

生成物 1

HCID 594143782-(perfluorophenoxy)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile収率 31%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(Methylthio)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (150 mg, 0.31 mmol) was dissolved in dichloromethane at room temperature. Meta-chloroperbenzoic acid (110 mg, 0.64 mmol) was added in one portion and the reaction was stirred for 5 minutes. Pentafluorophenol (285 mg, 1.55 mmol) was added and the solution was stirred at room temperature for 3 hours. The crude mixture was washed with a diluted solution of sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a solid (60 mg, 31% yield).

後処理

  1. stirringthe solution was stirred at room temperature for 3 hours
  2. washThe crude mixture was washed with a diluted solution of sodium bicarbonate and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica gel by flash column chromatography

出典と根拠

ORDレコード
ord-998258ca017c4116b9667045a1ff24a8
出典データセット
uspto-grants-2013_09
特許番号
US08530489B2

関連ノート

読み込み中…