Purge with nitrogen for five min a mixture of (4-bromo-2-nitro-phenyl)-(1-methyl-azetidin-3-yl)-amine (709 μmol, 203 mg), (E)-3,7-difluoro-11-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-ylmethylene)-6,11-dihydro-dibenzo[b,e]oxepine (723 μmol, 268 mg) in methanol (1.0 mL)/tetrahydrofuran (3.0 mL) (1:3 solvent ratio) in a sealed tube. Add sodium methoxide (1.42 mmol, 77 mg), tetrakis(triphenylphosphine)palladium (35 μmol, 41 mg) and heat at 70° C. overnight. Dilute with ethyl acetate, wash with 10% sodium bicarbonate twice, dry over anhydrous sodium sulfate, filter, and concentrate in vacuo to obtain 377 mg of an orange oil residue. Purify on a 12 g silica gel column eluting with 5% methanol in dichloromethane to obtain the title compound (199 mg, 62%). LC-MS m/z 450.0 [M+H]+.
