4-Bromo-2-methoxyphenol → HCID 57413730, compound
Reaction equation
CNC(=O)C1C=CC=C(C2C=CC(O[C@@H:17]3[C@@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]3)=C(C)C=2)C=1.Br[C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([O:38][CH3:39])[CH:32]=1.[CH3:40][O:41][C:42]([C:44]1[CH:45]=[C:46](B(O)O)[CH:47]=[CH:48][CH:49]=1)=[O:43]>>[CH3:39][O:38][C:33]1[CH:32]=[C:31]([C:48]2[CH:49]=[C:44]([CH:45]=[CH:46][CH:47]=2)[C:42]([O:41][CH3:40])=[O:43])[CH:36]=[CH:35][C:34]=1[O:37][C@@H:17]1[C@@H:22]([OH:23])[C@@H:21]([OH:24])[C@H:20]([OH:25])[C@@H:19]([CH2:26][OH:27])[O:18]1Participants
Procedure
4e was prepared using the same procedure as for 5b. In the first step of glycosidation reaction 4-bromo-2-methoxyphenol was used as glycosidation acceptor and in the second step of Suzuki coupling reaction 3-methoxycarbonylphenyl boronic acid was used instead. All intermediates were directly taken to the next step reaction without further purification. 4e was further purified by HPLC(C18, 15*150 mm column; eluent: acetonitrile/water (0.1% TFA)). Yield: 3%. 1H NMR (300 MHz, METHANOL-d4) δ ppm 8.21 (t, J=1.51 Hz, 1H), 7.96 (td, J=1.44, 7.83 Hz, 1H), 7.84 (ddd, J=1.24, 1.92, 7.83 Hz, 1H), 7.49-7.61 (m, 1H), 7.30 (d, J=8.24 Hz, 1H), 7.24 (d, J=1.92 Hz, 1H), 7.13-7.21 (m, 1H), 5.47 (d, J=1.92 Hz, 1H), 4.11 (dd, J=1.79, 3.43 Hz, 1H), 3.94 (s, 3H), 3.92 (s, 3H), 3.86-4.03 (m, 1H), 3.67-3.86 (m, 4H). MS (ESI): found [M+Na]+, 443.1.
Workup
- customAll intermediates were directly taken to the next step reaction without further purification
- custom4e was further purified by HPLC(C18, 15*150 mm column
Sources & evidence
- ORD record
- ord-acfdeb6f8146473c8d5a717ccbef1ae6
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937167B2
Reaction notes
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