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.O[C:26]1([C:42]2[CH:43]=[C:44]3[C:48](=[CH:49][C:50]=2[OH:51])[CH2:47][CH2:46][CH2:45]3)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]1=[O:41]>>[OH:51][C:50]1[CH:49]=[C:48]2[C:44]([CH2:45][CH2:46][CH2:47]2)=[CH:43][C:42]=1[CH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]1=[O:41]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-a225af3bf9104213818c3dbe741173ba
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Reaction notes
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