Evaluation of kilogram-scale Sonagashira, Suzuki, and Heck coupling routes to oncology candidate CP-724,714

被引：55

作者：

Ripin, DHB ^{[1
]}

Bourassa, DE ^{[1
]}

Brandt, T ^{[1
]}

Castaldi, MJ ^{[1
]}

Frost, HN ^{[1
]}

Hawkins, J ^{[1
]}

Johnson, PJ ^{[1
]}

Massett, SS ^{[1
]}

Neumann, K ^{[1
]}

Phillips, J ^{[1
]}

Raggon, JW ^{[1
]}

Rose, PR ^{[1
]}

Rutherford, JL ^{[1
]}

Sitter, B ^{[1
]}

Stewart, AM ^{[1
]}

Vetelino, MG ^{[1
]}

Wei, LL ^{[1
]}

机构：

[1] Pfizer Inc, Pfizer Global Res Div, Chem Res & Dev, Groton, CT 06340 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2005年 / 9卷 / 04期

关键词：

D O I：

10.1021/op050039u

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of the anti-cancer compound 2-methoxy-N-(3-{4-[3-methyl-4-(6-methyl-pyridin-3-yloxy)phenylamino]quinazolin-6-yl}-E-allyl)acetamide (CP-724,714) (1) on multikilogram scale using several different synthetic routes is described. Application of the Sonogashira, Suzuki, and Heck couplings to this synthesis was investigated to identify a safe, environmentally friendly, and robust process for the production of this drug candidate. A convergent and selective synthesis of the candidate was identified which utilizes a Heck coupling of a protected allylamine to install the critical olefin.

引用

页码：440 / 450

页数：11

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