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Two robust, efficient syntheses of [phenyl ring-U-14C]indole through use of [phenyl ring-U-14C]aniline

✍ Scribed by Carrie A. B. Wager; Sandra A. Miller

Publisher
John Wiley and Sons
Year
2006
Tongue
French
Weight
147 KB
Volume
49
Category
Article
ISSN
0022-2135

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✦ Synopsis

Two robust, efficient syntheses of [phenyl ring-U-14 C]indole are presented. In the first synthesis, we developed optimum reaction conditions for the Houben-Hoesch alkylation of chloro acetonitrile with aniline. This was found through the screening of several Lewis acids coupled with the use of Sugasawa conditions for ortho direction. Following alkylation, the resultant imine was hydrolyzed to the phenone, and then thermal cyclization followed by reduction led to indole. In the second synthesis of [phenyl ring-U-14 C]indole, we utilized microwave-enhanced conditions for the key coupling. In this transformation, aniline was alkylated with the acetal of bromo acetaldehyde. The mono-alkylated aniline was then transformed in a straightforward manner to indole.

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