2-Methyltetrahydrofuran → US9000184, 6, isomer 1

Participants

Reaction Conditions

Reaction Steps

7′-Bromo-4-methoxy-5″-methyl-3′,4′-dihydrodispiro[cyclohexane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 5, 0.184 g, 0.47 mmol), 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (0.122 g, 0.47 mmol), 3-(di-tert-butylphosphonium)propane sulfonate (0.013 g, 0.05 mmol), sodium tetrachloropalladate(II) (6.95 mg, 0.02 mmol), 2-methyltetrahydrofuran (3 mL) and potassium carbonate (2.0 M, 0.708 mL, 1.42 mmol) were added to a microwave vial. The vial was sealed and heated with MW for 30 min at 130° C. The same amount of ligand and Pd-catalyst were added again and the reaction was heated in the MW for 15 min at 130° C. Water and 2-Me THF was added and the water phase was eliminated. The organic phase was washed once with brine and once with water. The organic phase was concentrated in vacuo. The product was purified using prep HPLC. Fractions containing the isomeric products were collected separately and the MeOH was evaporated. DCM was added and the mixture was poured into a phase separator. The organic phase was concentrated in vacuo to give:

Provenance & Evidence