HRID21306

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID176

Acetic Acid

C2H4O2

HCID6342

Acetonitrile

C2H3N

HCID8021

Diethylamine

C4H11N

HCID5049666

Sodium triacetoxyborohydride

C6H10BNaO6

结构：COc1cc(-c2cc3c(C=O)cccc3n2C(=O)OC(C)(C)C)c2c(c1OS(C)(=O)=O)CNC2=O

HCID86628325

未命名化合物

PRODUCTS

生成物

结构：CCN(CC)Cc1cccc2c1cc(-c1cc(OC)c(OS(C)(=O)=O)c3c1C(=O)NC3)n2C(=O)OC(C)(C)C

HCID86628326

未命名化合物

收率 57%

PROCEDURE

实验过程

In a similar manner to Step 2 of Example 6, 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-formylindol-2-yl]isoindolinone (0.226 g, 0.452 mmol) was dissolved in acetonitrile (15.0 mL) and the solution was treated with diethylamine (0.935 mL, 9.03 mmol), acetic acid (0.517 mL, 9.03 mmol) and sodium triacetoxyborohydride (0.479 g, 2.26 mmol), followed by purification of the residue by flash column chromatography (chloroform/methanol=3/1) to obtain 4-methanesulfonyloxy-5-methoxy-7-[1-(tert-butoxycarbonyl)-4-(diethylaminomethyl)indol-2-yl]isoindolinone (0.144 g, 57%).

WORKUP

后处理

customfollowed by purification of the residue by flash column chromatography (chloroform/methanol=3/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-d869d32971364482a916dc88fae8025d
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07745641B2
来源说明: uspto-grants-2010_06

反应 SMILES

[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH:26]=O)[CH:22]=[CH:21][CH:20]=3)=[C:11]2C=1CN[C:10]2=[O:35])(=[O:4])=[O:3].[CH2:36]([NH:38][CH2:39][CH3:40])[CH3:37].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:59](#[N:61])[CH3:60]>>[CH3:1][S:2]([O:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([C:17]2[N:18]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:19]3[C:24]([CH:25]=2)=[C:23]([CH2:26][N:38]([CH2:39][CH3:40])[CH2:36][CH3:37])[CH:22]=[CH:21][CH:20]=3)=[C:11]2[C:60]=1[CH2:59][NH:61][C:10]2=[O:35])(=[O:4])=[O:3]