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■ Synthesis of Benzo[de]chromene Analogue of Efaroxan

Patrice Mayer,* Sonia Alibert, Pascale Brunel, and Thierry Imbert

*Division de Chimie Médicinale III, Institut de Recherche Pierre Fabre, 17, avenue Jean Moulin, F-81106 Castres Cedex 06, France

Abstract

2-(2-Ethyl-2,3-dihydro-benzo[de]chromen-2-yl)-4,5-dihydro-1H-imidazole (2) was synthesized in seven steps starting from 3-methylanthranilic acid (3). The key intermediate 8-bromomethyl-4-bromonaphthoxybutyrate (8) was obtained starting from 8-methyl-1-naphthol (5b). The target molecule is a benzo[de]chromene analogue of efaroxan (1), a potent and selective antagonist of α₂-adrenoceptors.