Sodium Carbonate → Ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate

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Reaction Steps

To a solution of ethyl 7-(trifluoromethylsulfonyloxy)-3-azabicyclo[3.3.1] non-6-ene-3-carboxylate (0.13 g, 0.38 mmol) in dimethoxyethane (3 mL) was added saturated sodium carbonate solution (1 mL), lithium chloride (0.04 g, 0.9 mmol) and 5-phenoxy-3-pyridinylboronic acid (0.17 g, 0.79 mmol). The flask was alternately evacuated and filled with argon three times. Then, tetrakis(triphenylphosphine)palladium(0) (0.01 g, 0.01 mmol) was added, and the evacuation and argon fill was performed once again. The flask was sealed under argon, and the stirred reaction mixture was heated at 95(C for 2 h. The mixture was cooled to ambient temperature, diluted with water (10 mL), extracted with chloroform (3×5 mL). The extracts were dried over sodium sulfate and filtered. Concentration of the filtrate by rotary evaporation, followed by purification of the residue by silica gel column chromatography, using a gradient of 0-2% methanol in chloroform/as eluent, gave ethyl 7-(5-phenoxy-3-pyridinyl)-3-azabicyclo[3.3.1]non-6-ene-3-carboxylate as a light yellow oil (0.12 g, 87%).

Provenance & Evidence