3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl [3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate
Reaction equation
BrC1C=CC(O)=C(C2(O)C3C(=CC=CC=3)N(CCCCC)C2=O)C=1.[CH2:25]([O:27][C:28](=[O:51])[CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](O)([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][C:47]=2[OH:48])[CH2:44][CH2:43][CH2:42]3)[C:31]1=[O:50])[CH3:26]>>[CH2:25]([O:27][C:28](=[O:51])[CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]([C:39]2[CH:40]=[C:41]3[C:45](=[CH:46][C:47]=2[OH:48])[CH2:44][CH2:43][CH2:42]3)[C:31]1=[O:50])[CH3:26]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in PREPARATION 15B, and making non-critical variations to replace 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one with ethyl[3-hydroxy-3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained: 1H NMR (300 MHz, CDCl3) δ 8.50-7.90 (br, 1H), 7.40-7.32 (m, 2H), 7.38 (td, 1H), 6.94 (s, 1H), 6.84 (d, 1H), 6.75 (s, 1H), 5.16 (s, 1H), 4.48 (ABq, 2H), 4.21 (q, 2H), 2.85 (t, 2H), 2.81-2.61 (m, 2H), 2.09-1.92 (m, 2H), 1.25 (t, 3H); MS (ES+) m/z 352 (M+1).
Sources & evidence
- ORD record
- ord-00548c77a3a44b2c95815d623712d5e4
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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