3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 7-(3-Chloro-4-fluorophenyl)-5-ethyl-5-thien-3-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH2:18][CH3:19])([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[C:6]=2[CH:20]=1.[Cl:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[F:28]>>[Cl:21][C:22]1[CH:23]=[C:24]([C:2]2[CH:3]=[CH:4][C:5]3[NH:11][C:10](=[O:12])[CH2:9][O:8][C:7]([CH2:18][CH3:19])([C:13]4[CH:17]=[CH:16][S:15][CH:14]=4)[C:6]=3[CH:20]=2)[CH:25]=[CH:26][C:27]=1[F:28]Participants
3
Procedure
Prepared from 7-bromo-5-ethyl-5-thien-3-yl-1,5-dihydro-4,1-benzoxazepin-2(3H)-one and 3-chloro-4-fluorobenzeneboronic acid using the coupling procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.03 (s, 1H), 7.84 (dd, J=6.9, 2.2 Hz, 1H), 7.62 (m, 2H), 7.56 (dd, J=5.2, 3.0 Hz, 1H), 7.48 (m, 2H), 7.27 (m, 1H), 7.24 (d, J=8.5 Hz, 1H), 7.16 (dd, J=5.2, 1.4 Hz, 1H), 4.04 (d, J=15.4 Hz, 1H), 3.94 (d, J=15.4 Hz, 1H), 2.53 (m, 1H), 2.35 (m, 1H), 0.75 (t, J=7.1 Hz, 3H); MS (ES) m/z 402 (M+H)+;
Sources & evidence
- ORD record
- ord-0c2a88da5bfa4091b78e60b753710879
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598237B2
Reaction notes
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