HRID1668673

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11430

Potassium Carbonate

CK2O3

HCID192734

5-Hydroxy-3-methylindole

C9H9NO

结构：COc1cc2c(Cl)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1

HCID21936046

未命名化合物

PRODUCTS

生成物

结构：COc1cc2c(Oc3ccc4[nH]cc(C)c4c3)ncnc2cc1OCC1CCN(C(=O)OC(C)(C)C)CC1

HCID22030599

未命名化合物

收率 99.2%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 90 °C

PROCEDURE

实验过程

A mixture of 7-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methoxy}-4-chloro-6-methoxyquinazoline (4.6 g), 5-hydroxy-3-methylindole (2 g), (Journal of Organic Chemistry 1993, 58, 3757), potassium carbonate (3.1 g) and DMF (20 ml) was stirred and heated to 90° C. for 2 hours. The solid was removed by filtration washed with acetonitrile and the combined filtrates concentrated to dryness under vacuum. The product so obtained was triturated under ether/petroleum ether (8/2), collected by filtration and dried to give 7-{[1-(tert-butoxycarbonyl)piperidin-4-yl]methoxy}-6-methoxy-4-[(3-methyl-1H-indol-5-yl)oxy]quinazoline (5.8 g).

WORKUP

后处理

customThe solid was removed by filtration
washwashed with acetonitrile
concentrationthe combined filtrates concentrated to dryness under vacuum
customThe product so obtained
customwas triturated under ether/petroleum ether (8/2)
filtrationcollected by filtration
customdried

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8a4ab405018a40e089e54074614fd02c
来源数据集: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07989460B2
来源说明: uspto-grants-2011_08

反应 SMILES

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20](Cl)=[N:21][CH:22]=[N:23]3)=[CH:18][C:17]=2[O:27][CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][CH:34]=[C:33]2[CH3:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([O:29][C:30]4[CH:31]=[C:32]5[C:36](=[CH:37][CH:38]=4)[NH:35][CH:34]=[C:33]5[CH3:39])=[N:21][CH:22]=[N:23]3)=[CH:18][C:17]=2[O:27][CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]