In a 1-dram vial, mix 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenylboronic acid (100 mg, 0.307 mmol), chloropyrazine (69 mg, 0.460 mmol), cesium fluoride (94 mg, 0.614 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (1:1 complex with CH2C2, 25 mg, 0.031 mmol) in dioxane (2 mL). Heat to 85° C. for 72 h, then remove solvent under nitrogen. Take up the resulting residue in H2O (1 mL) and CH2Cl2 (1 mL) and load onto a Varian ChemElut CE1005 solid-phase extraction cartridge. Elute, collect, and concentrate 15 mL CH2Cl2 to obtain crude product. Purify by mass-guided reverse-phase HPLC to obtain 2.3 mg (2%) of the title compound. MS (ES) 361 (M+H); HPLC shows 93% purity.
