反応式
[Cl:1][C:2]1[C:10](OS(C(F)(F)F)(=O)=O)=[CH:9][C:8]([C:19]2[N:20]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[CH:23][CH:22]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:42].[CH2:43]([Zn]CC)[CH3:44].C1(C)C=CC=CC=1.O>C(COC)OC>[Cl:1][C:2]1[C:10]([CH2:43][CH3:44])=[CH:9][C:8]([C:19]2[N:20]([C:35]([O:37][C:38]([CH3:41])([CH3:39])[CH3:40])=[O:36])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([CH2:28][N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)=[CH:23][CH:22]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:42]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 90 °C
実験手順
4-Chloro-5-trifluoromethanesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (93.5 mg, 0.149 mmol) was dissolved in dimethoxyethane (4.7 mL), and the solution was added with 1.1 mmol/L diethyl zinc-toluene solution (0.68 mL, 0.744 mmol) and [bis(diphenylphosphino)ferrocene]dichloropalladium (34.4 mg, 0.030 mmol), followed by stirring at 90° C. for 12 hours under argon atmosphere. The reaction mixture was added with water and filtered using Celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with saturated brine, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=6/1) to obtain 4-chloro-5-ethyl-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (39.0 mg, yield 52%).
後処理
- filtrationfiltered
- extractionThe filtrate was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialby drying over sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=6/1)
出典と根拠
- ORDレコード
- ord-511ca781d3724bffb5bb46b310d5c8f5
- 出典データセット
- uspto-grants-2010_06
- 特許番号
- US07745641B2
関連ノート
読み込み中…