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Note | Regular issue | Vol 48, No. 12, 1998, pp.2669-2675
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8342
A Convenient Synthesis of 2-Phenylbenzofuran Derivatives with Potent Testosterone 5α-Reductase Inhibitory Activities

Koki Ishibashi, Katsuyoshi Nakajima, and Takahide Nishi*

*Medicinal Chemistry Research Laboratories, Sankyo Co. Ltd., 5-14-21 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan

Abstract

A convenient method for the synthesis of 4-[2-(benzo[b]furan-2-yl)phenyloxy]butyric acid derivatives with a carbamoyl group at the 5 or 6 position of the benzofuran ring showing potent 5α-reductase inhibitory activities was developed. Oxazolin-2-ylbenzofuran derivatives were treated with tert-BuLi followed by tri(n-butyl)tin chloride, to give 2-tri(1-butyl)stannylbenzofuran derivatives. A palladium-catalyzed cross-coupling reaction of these benzofuran derivatives with tert-butyl 4-(2-iodophenyloxy)butyrate afforded the 2-phenyl benzofuran compounds in good yields.