5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one → 5-(3-Fluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

Following procedures essentially as described in Example 219, using 11-bromomethylene-3-fluoro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 1.05 eq.) and 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (1 eq.). Purify crude product on silica gel, eluting with 60% to 100% ethyl acetate/CHCl3 to afford a light yellow solid. Triturate with acetone to afford the title compound as a white solid. HPLC (ISO60-10) t=4.09 min, 100%; MS [ES] 357 (M−H), 359 M+H); 1H-NMR (DMSO-d6) δ 10.56 (s, 1H), 10.46 (s, 1H), 7.56 (m, 2H), 7.35 (t, 1H, J=7.5 Hz), 7.23 (t, 1H, J=7.5 Hz), 6.99 (d, 1H, J=7.5 Hz), 6.94 (s, 1H), 6.78 (td, 1H, J=12.0, 4.2 Hz), 6.71 (d, 1H, J=8.4 Hz), 6.66 (d, 1H, J=8.4 Hz), 6.59 (dd, 1H, J=10.6, 2.6 Hz), 6.57 (s, 1H), 5.83-4.71 (br d, 2H).

Provenance & Evidence