Sodium Carbonate → 1-(1,1-Dimethyl-2-morpholin-4-yl-ethyl)-5-(3-fluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

Mix 1-(1,1-dimethyl-2-morpholin-4-yl-ethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (900 mg of 60% purity, 1.34 mmol), 11-bromomethylene-3-fluoro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 520 mg, 1.7 mmol), 2N Na2CO3 (4 mmol) in dioxane (10 mL). Sparge with nitrogen for 10 min and then add tetrakistriphenylphosphine Pd (0) (98 mg, 0.08 mmol) and heat at 90-100° C. 5 days. Cool the reaction and shake with water/EtOAc. Dry (MgSO4) and concentrate to give 1.05 g crude product. Purify by column chromatography using 2% 2N NH3 in MeOH/methylene chloride to give 400 mg (80%) title compound as an off-white solid. MS (es) 500 (M+1), 498 (M−1); HPLC (ISO80-10M) t=1.95 min (100%); 1NMR (CDCl3) 8.17 (s, 1H), 7.49 (t, 1H, J=7.5 Hz), 7.46 (d, 1H, J=7.0 Hz), 7.37 (t, 1H, J=7.0 Hz), 7.26 (t, 1H, J=7.5 Hz), 7.14 (d, 1H, J=7.5 Hz), 6.91 (d, 1H, J=8.5 Hz), 6.89 (s, 1H), 6.81 (d, 1H, J=7.5 Hz), 6.70 (td, 1H, J=11.7, 4.1 Hz), 6.66 (s, 1H), 6.56 (dd, 1H, J=10.1, 2.6 Hz), 6.03-4.76 (br d, 2H), 3.85-3.70 (m, 6H), 2.73 (t, 4H, J=4.2 Hz), 1.13 (s, 6H).

Provenance & Evidence