Tetrabutylammonium Fluoride → 5-Methyl-6-(1,4-dioxaspiro[4.5]dec-7-EN-8-YL)pyridin-3-amine

Participants

Reaction Conditions

Reaction Steps

1.0M Toluene-solution of lithium bis(trimethylsilyl)amide (13.4 ml) was added at room temperature under nitrogen atmosphere to a solution of 5-bromo-2-(1,4-dioxaspiro[4,5]decane-7-ene-8-yl)-3-methylpyridine (2.78 g) of Reference Example 105, bis(dibenzylideneacetone) palladium (0) (258 mg) and tri-tert-butylphosphine tetrafluoroborate (130 mg) in toluene (12 ml), and stirred at 70° C. for two hours. Then, the reaction solution was cooled to room temperature, 1.0M tetrahydrofuran-solution of tetrabutylammonium fluoride (40.3 ml) was added and stirred at the same temperature for an hour. After completion of the reaction, water was added to the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with basic silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (773 mg) as a pale yellow solid.

Provenance & Evidence