Sodium Carbonate → 5-(3-Chloro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

Following procedures essentially as described in Example 219, mix 11-bromomethylene-3-chloro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 40 mg, 0.124 mmol) (prepared essentially as described in Preparation 55), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (31 mg, 0.118 mmol), Na2CO3 (2M in water, 148 □L, 0.295 mmol), dioxane (1 mL), and Pd(PPh3)4 (7 mg, 0.006 mmol). Purify the crude product on silica gel (12 g) eluting with 2% to 5% (2M NH3/MeOH)/CH2Cl2 to afford 31 mg (69%) of the title compound as a white solid. HPLC (ISO80-10) t=2.85min, 99%; MS [ES] 373 (M−H); 1H-NMR (DMSO-d6) 10.57 (s, 1H), 10.47 (s, 1H), 7.56 (dd, 2H, J=7.8, 6.1 Hz), 7.35 (t, 1H, J=7.5 Hz), 7.24 (t, 1H, J=7.7 Hz), 6.98 (m, 3H), 6.82 (d, 1H, J=4.4 Hz), 6.69 (m, 2H), 6.57 (s, 1H), 5.89-4.79 (br d, 2H).

Provenance & Evidence