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An Efficient One-Pot Process for 10-Bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one, an Intermediate to SCH 66336
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2003-08-12 , DOI: 10.1021/op034054f Xiaoyong Fu 1 , Timothy L. McAllister 1 , Xiongwei Shi 1 , T. K. Thiruvengadam 1 , Chou-Hong Tann 1 , Junning Lee 1
Organic Process Research & Development ( IF 3.1 ) Pub Date : 2003-08-12 , DOI: 10.1021/op034054f Xiaoyong Fu 1 , Timothy L. McAllister 1 , Xiongwei Shi 1 , T. K. Thiruvengadam 1 , Chou-Hong Tann 1 , Junning Lee 1
Affiliation
An efficient process for the preparation of 10-bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (7), an intermediate to an antitumor agent SCH 66336, is described. This one-pot method consists of a selective reduction of 8-chloro-7(9)-nitro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (4) with Sn(II) bromide (generated in situ from Sn(II) sulfate and HBr), followed by bromination at the 10 position, and deamination. The desired product (7) is isolated in 75% overall yield.
中文翻译:
10-Bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one(SCH 66336 的中间体)的高效一锅法
一种制备抗肿瘤剂中间体 10-bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (7) 的有效方法SCH 66336 进行了描述。这种一锅法包括选择性还原 8-chloro-7(9)-nitro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (4)用溴化 Sn(II)(由硫酸 Sn(II) 和 HBr 原位生成),然后在 10 位溴化,然后脱氨。所需产物 (7) 以 75% 的总产率分离。
更新日期:2003-08-12
中文翻译:
10-Bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one(SCH 66336 的中间体)的高效一锅法
一种制备抗肿瘤剂中间体 10-bromo-8-chloro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (7) 的有效方法SCH 66336 进行了描述。这种一锅法包括选择性还原 8-chloro-7(9)-nitro-5,6-dihydro-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one (4)用溴化 Sn(II)(由硫酸 Sn(II) 和 HBr 原位生成),然后在 10 位溴化,然后脱氨。所需产物 (7) 以 75% 的总产率分离。