Potassium Carbonate → HCID 71270799, compound

Participants

Reaction Steps

A solution of methyl 3-(4-bromo-2-fluorophenyl)-3-(4-cyclopropyl-3-oxo-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)propanoate (1.924 mmol) in 1,4-dioxane (6 mL) was treated with 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (2.116 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.096 mmol) and 2M aq potassium carbonate (5.77 mmol). The reaction vessel was purged with nitrogen and sealed, and the mixture was irradiated in a Biotage Initiator Microwave at 120° C. for 15 min. The resulting black mixture was diluted with water (50 mL) and extracted with dichloromethane three times. The combined organic layer was treated with Silicycle Si-thiol (100 mg), dried over sodium sulfate, filtered and concentrated in vacuo. Purification of the residue by silica gel chromatography (0-7% methanol/dichloromethane) afforded the title compound as a brown solid (802 mg, 72% yield). MS(ES)+ m/e 518.4 [M+H]+.

Provenance & Evidence