Journal of fluorine chemistry

Polyfluoroaralkylamines: an improved synthesis of 4, 5, 6, 7-tetrafluoroindole

R Filler, W Chen, SM Woods

Index: Filler, Robert; Chen, Wei; Woods, Sarah M. Journal of Fluorine Chemistry, 1995 , vol. 73, # 1 p. 95 - 100

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Citation Number: 13

Abstract

Tetrafluoroindole (5), a precursor for potential biologically-active compounds, was prepared previously in a four-step synthesis from C6F6. However, catalytic reduction of pentafluorophenylacetonitrile (2) to 2-pentafluorophenylethyl amine (3) is accompanied by a significant amount of a secondary amine, which, like 3, undergoes cyclization to an indoline and subsequent dehydrogenation to a new indole 8. The side-reaction in the reduction of ...