Reaction Steps
Following procedures essentially as described in Example 219, mix 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (535 mg, 2.06 mmol) (prepared from 5-bromo-1,3-dihydro-benzoimidazol-2-one (Preparation 27) according to the procedure reported by M Murata, T Takashi, S Watanabe and Y Yusuru, J. Org. Chem.; 65 (1) 164-168 (2000)), 5-bromomethylene-2,8-difluoro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (550 mg, 1.71 mmol), 2N Na2CO3 (2 mL), dioxane (14 mL) and (Ph3P)4Pd (200 mg, 0.17 mmol). Purify the crude product by column chromatography using dichloromethane/ethyl acetate to give 285 mg white solid, mp 257° C. HPLC (ISO80-10M) t=2.62 (97%), MS (ES) 373 (M−1). H NMR 10.55 (s, 1H), 10.45 (s, 1H), 7.48 (dd, 1H, J=8.4, 6.2 Hz), 7.21 (dd, 1H, J=9.7, 2.2 Hz), 7.01 (td, 1H, J=12.2, 4.2 Hz), 6.94 (dd, 1H, J10.1, 2.2 Hz), 6.90 (d, 2H, J=6.2 Hz), 6.85 (dd, 1H, J=8.6, 2.4 Hz), 6.78 (s, 1H), 6.72 (d, 1H, J=8.4 Hz), 6.67 (d, 1H, J=7.9 Hz), 6.51 (s, 1H), 3.30 (s, 2H), 2.89 (s, 2H), 6.90 (d, 1H, J=6.2 Hz).
