Potassium Carbonate → 2-(4-Cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)-2-(4-(quinolin-7-yl)phenyl)acetic acid

Beteiligte Stoffe

Reaktionsschritte

A solution of 2-(4-bromophenyl)-2-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)acetic acid (0.402 mmol) in 1,4-dioxane (2 mL) and ethanol (0.2 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (0.442 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.020 mmol) and 2M aq potassium carbonate (0.602 mL). The vessel was purged with nitrogen, sealed and the reaction irradiated in a Biotage Initiator microwave at 120° C. for 10 min. The resulting black solution was then diluted with water (50 mL) and brine (10 mL), and the aqueous solution was sequentially extracted with dichloromethane and tetrahydrofuran. Only the tetrahydrofuran layer contained the product. The aqueous layer was concentrated in vacuo and the resulting solid was triturated with ethanol. The ethanol solution was filtered and added to the tetrahydrofuran layer. This organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the crude material by reverse phase HPLC (10-35% acetonitrile/water with 0.1% NH4OH) afforded the title compound as a white solid (32%). MS(ES)+ m/e 472.4 [M+H]+.

Herkunft & Nachweise