Synthesis of an Ethyl 6-Amino-3,5-difluorosalicylate Derivative
by Sequential Regioselective Directed ortho-Metalation,
A Practical Synthesis of4,5-Diamino-3,6,8-trifluoroflavone, A Potent Antitumor Agent

Tsutomu Akama; Kimihisa Ueno; Hiromitsu Saito; Masaji Kasai

doi:10.1055/s-1997-1379

Synthesis 1997; 1997(12): 1446-1450
DOI: 10.1055/s-1997-1379

paper

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Synthesis of an Ethyl 6-Amino-3,5-difluorosalicylate Derivative by Sequential Regioselective Directed ortho-Metalation; A Practical Synthesis of4',5-Diamino-3',6,8-trifluoroflavone, A Potent Antitumor Agent

Tsutomu Akama¹ , Kimihisa Ueno, Hiromitsu Saito, Masaji Kasai²

¹Pharmaceutical Research Laboratories, Kyowa Hakko Kogyo Co. Ltd., 1188 Shimotogari, Nagaizumi-cho, Shizuoka 411, Japan, Fax +81(427)268330; E-mail: tsutomu.akama@kyowa.co.jp
²Pharmaceutical Research Laboratories, Kyowa Hakko Kogyo Co. Ltd., 1188 Shimotogari, Nagaizumi-cho, Shizuoka 411, Japan, Fax +81(427)268330

Abstract

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The multigram scale synthesis of 4',5-diamino-3',6,8-trifluoroflavone, a potent antitumor agent, is described in which regioselective introduction of a carbonyl group into the ortho-position to the amide group of 2-[2,4-difluoro-5-(pivaloylamino)phenoxy]tetrahydropyran is achieved by using sequential direct ortho-metalations as the key step.

directed ortho-metalation - Stille coupling - flavone

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