9-Methyl-3,9-diazabicyclo[3.3.1]nonane → 3-(6-Methoxy-naphthalen-2-yl)-9-methyl-3,9-diaza-bicyclo[3.3.1]nonane Fumaric Acid Salt

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Reaction Steps

A mixture of 9-methyl-3,9-diaza-bicyclo[3.3.1]nonane (2.0 g, 14.3 mmol), 2-bromo-6-methoxynaphthalene (5.07 g, 21.4 mmol), palladacycle (100 mg, 0.11 mmol), potassium tert-butoxide (3.2 g, 28.5 mmol) and dioxane (30 ml) was stirred at reflux for 40 h. The mixture was cooled to room temperature. Water (50 ml) was added and the mixture was extracted with ethylacetate (3×30 ml). The crude product was purified by silica gel column chromatography using a solvent mixture of dichloromethane, methanol and aqueous ammonia (18:1:1%). The fumarate salt was precipitated from 1.1 eq of fumaric acid and a mixture of ethanol and diethylether (2:5). Yield 1.4 g (33%). Mp 190.0-198.3° C. LC-ESI-HRMS of [M+H]+ shows 297.1955 Da. Calc. 297.196688 Da, dev. −4 ppm.

Provenance & Evidence