HRID40106

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID3301

Ethylenediamine

C2H8N2

HCID67184

1-Bromopyrrolidine-2,5-dione

C4H4BrNO2

结构：CC(C)Oc1ccc2c(C(=O)NCc3ccc(F)c(F)c3)c(C=O)n(Cc3ccccn3)c2c1

HCID59762313

未命名化合物

2 次

PRODUCTS

生成物

结构：CC(C)Oc1ccc2c(C(=O)NCc3ccc(F)c(F)c3)c(C3=NCCN3)n(Cc3ccccn3)c2c1

HCID59762307

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

PROCEDURE

实验过程

To a solution of N-(3,4-difluorobenzyl)-2-formyl-6-isopropoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 105, 27 mg, 0.058 mmol) in CH2Cl2 (2 ml) was added 1,2-ethylene-diamine (5 μl, 0.070 mmol). The reaction was stirred at room temperature for 1 h and NBS (13 mg, 0.070 mmol) was added. The reaction was stirred for 16 h and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel (9:1 EtOAc-Et3N, then 8:2:1 EtOAc-MeOH-Et3N) followed by PTLC eluted with EtOAc to yield the title compound.

WORKUP

后处理

stirringThe reaction was stirred for 16 h
customthe solvent was removed in vacuo
customThe residue was purified by chromatography on silica gel (9:1 EtOAc-Et3N
washeluted with EtOAc

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-aca7d67b53214ed7ad76bd4b06e6972f
来源数据集: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08524917B2
来源说明: uspto-grants-2013_09

反应 SMILES

[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[CH:29]=O)=[O:8].[CH2:35]([NH2:38])[CH2:36][NH2:37].C1C(=O)N(Br)C(=O)C1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][C:33]=1[F:34])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH:19]([CH3:20])[CH3:21])=[CH:15][CH:16]=2)[N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:10]=1[C:29]1[NH:37][CH2:36][CH2:35][N:38]=1)=[O:8]