HRID21325

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10796

Cesium carbonate

CCs2O3

HCID81363

1-Chloro-3-iodopropane

C3H6ClI

结构：Cc1c(-c2cc(O)c(Cl)c3c2C(=O)NC3)n(C(=O)OC(C)(C)C)c2ccc(CN3CCCCC3)cc12

HCID86628332

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)n1c(-c2cc(OCCCCl)c(Cl)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21

HCID68491846

未命名化合物

收率 84.5%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6342

Acetonitrile

C2H3N

PROCEDURE

实验过程

In a similar manner to Step 1 of Example 433, 4-chloro-5-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)methylindol-2-yl]isoindolinone (100 mg, 0.202 mmol) was suspended in acetonitrile (5.0 mL), and the suspension was treated with cesium carbonate (98.7 mg, 0.303 mmol) and 1-chloro-3-iodopropane (0.026 mL, 0.242 mmol), followed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1) to obtain 4-chloro-5-(3-chloropropoxy)-7-[1-(tert-butoxycarbonyl)-5-(piperidin-1-ylmethyl)indol-2-yl]isoindolinone (97.7 mg, yield 84%).

WORKUP

后处理

customfollowed by purification by flash column chromatography (chloroform/methanol=19/1, 4/1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-934a2d9f73474745bfc5b298c065623f
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

[Cl:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([C:12]2[N:13]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:14]3[C:19]([C:20]=2C)=[CH:18][C:17]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:43][CH2:44][CH2:45][CH2:46]I>C(#N)C>[Cl:1][C:2]1[C:10]([O:11][CH2:46][CH2:45][CH2:44][Cl:43])=[CH:9][C:8]([C:12]2[N:13]([C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:16][CH:15]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:36]