3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl [3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-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:52])[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[C:48]([OH:49])=[CH:47][C:46]3[CH2:45][CH2:44][CH2:43][CH2:42][C:41]=3[CH:40]=2)[C:31]1=[O:51])[CH3:26]>>[CH2:25]([O:27][C:28](=[O:52])[CH2:29][N:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]([C:39]2[C:48]([OH:49])=[CH:47][C:46]3[CH2:45][CH2:44][CH2:43][CH2:42][C:41]=3[CH:40]=2)[C:31]1=[O:51])[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-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained: 1H NMR (300 MHz, CDCl3) δ 7.42-7.32 (m, 2H), 7.20 (t, 1H), 6.84 (d, 1H), 6.78 (s, 1H), 6.61 (s, 1H), 5.12 (s, 1H), 4.47 (ABq, 2H), 4.21 (q, 2H), 2.76-2.44 (m, 4H), 1.78-1.64 (m, 4H), 1.24 (t, 3H); MS (ES+) m/z 366 (M+1).
Sources & evidence
- ORD record
- ord-c77ab64bfa7f490eb8ce52ec62b47f0d
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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