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

Participants

Reaction Steps

Following procedures essentially as described in Example 219, mix 1-(2-morpholin-4-yl-propyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-benzoimidazol-2-one (205 mg, 0.53 mmol)(prepared following procedures essentially as described in Preparation 36), 11-bromomethylene-3-fluoro-6,11-dihydro-dibenzo[b,e]oxepine (E-isomer, 150 mg, 0.5 mmol), 2N Na2CO3 (0.5 mL), dioxane (5 mL) and (Ph3P)4Pd (53 mg, 0.046 mmol). Purify the crude product by column chromatography using 2N NH3 in MeOH/dichloromethane. Triturate the product obtained (192 mg) with hexane to give 170 mg pure title compound, HPLC (ISO80-10M) t=1.72 (100%). MS (ES) 486 (M+1), 484 (M−1). H NMR (DMSO-d6)10.68 (s, 1H), 7.57 (m, 2H), 7.35 (t, 1H, J=7.5 Hz), 7.22 (t, 1H, J=7.7 Hz), 6.96 (m, 3H), 6.78 (td, 1H, J=12.0, 4.2 Hz), 6.71 (d, 1H, J=7.5 Hz), 6.60 (m, 2H), 5.31 (br d, 2H), 3.72 (t, 2H, J=6.6 Hz), 3.46 (t, 4H, J=4.2 Hz), 2.48 (m, 4H), 1.71 (m, 2H), 2.20 (m, 6H).

Provenance & Evidence