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
Reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][O:6][C:5]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:4]1=2.CC1(C)C(C)(C)OB([C:27]2[CH:36]=[CH:35][C:30]3[NH:31][C:32](=[O:34])[NH:33][C:29]=3[CH:28]=2)O1>>[F:18][C:15]1[CH:16]=[CH:17][C:4]2[C:3](=[CH:2][C:27]3[CH:36]=[CH:35][C:30]4[NH:31][C:32](=[O:34])[NH:33][C:29]=4[CH:28]=3)[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[CH2:7][O:6][C:5]=2[CH:14]=1Participants
Procedure
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).
Workup
- customPurify crude product on silica gel
- washeluting with 60% to 100% ethyl acetate/CHCl3
- customto afford a light yellow solid
- customTriturate with acetone
Sources & evidence
- ORD record
- ord-0dc528f0707c4204bc8f13759e49df5e
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07411072B2
Reaction notes
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