Sodium Carbonate → 5-(3,7-Difluoro-6H-dibenzo[b,e]oxepin-11-ylidenemethyl)-1-(2-morpholin-4-yl-ethyl)-1,3-dihydro-benzoimidazol-2-one

Participants

Reaction Steps

Following procedures essentially as described in Example 219, mix 11-bromomethylene-3,7-difluoro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 200 mg, 0.619 mmol) (prepared essentially as described in Preparation 55), 1-(2-morpholin-4-yl-ethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (220 mg, 0.589 mmol), Na2CO3 (2M in water, 736 □L, 1.47 mmol), dioxane (4 mL), and Pd(PPh3)4 (36 mg, 0.031 mmol). Purify the crude product on silica gel (64 g) eluting with 2% (2M NH3/MeOH)/CH2Cl2 to afford 191 mg (66%) of the title compound as a white foam. HPLC (ISO80-10) t=1.95 min, 98%; MS [ES] 488 (M−H), 490 (M+H); 1H-NMR (DMSO-d6) δ 10.69 (s, 1H), 7.58 (dd, 1H, J=8.8, 7.0 Hz), 7.24 (m, 2H), 7.02 (s, 1H), 6.96 (d, 1H, J=8.4 Hz), 6.80 (m, 3H), 6.64 (m, 2H), 5.56-5.20 (br d, 2H), 3.81 (t, 2H, J=6.4 Hz), 3.46 (t, 4H, 4.4 Hz), 2.48 (m, 2H), 2.37 (s, 4H).

Provenance & Evidence