4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl [3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate
Reaction equation
BrC1C=CC=C2C=1C(C1C(O)=CC3OCOC=3C=1)[C:5](=[O:16])N2CCCCC.[CH2:27]([O:29][C:30](=[O:52])[CH2:31][N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]([C:41]2[C:49]([OH:50])=[CH:48][C:44]3[O:45][CH2:46][O:47][C:43]=3[CH:42]=2)[C:33]1=[O:51])[CH3:28]>>[CH2:27]([O:29][C:30](=[O:52])[CH2:31][N:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34]([C:41]2[C:49]([OH:50])=[CH:48][C:44]3[O:45][CH2:46][O:47][C:43]=3[CH:42]=2)([CH2:5][OH:16])[C:33]1=[O:51])[CH3:28]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in PREPARATION 1E, and making non-critical variations to replace 4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with ethyl[3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained as a white powder: 1H NMR (300 MHz, DMSO-d6) δ 9.03 (s, 1H), 7.17-6.85 (m, 5H), 6.22 (s, 1H), 5.83 (s, 2H), 5.04 (t, 1H), 4.56-4.08 (m, 5H), 3.69 (m, 1H), 1.18 (t, 3H); MS (ES+) m/z 408.1 (M+23).
Sources & evidence
- ORD record
- ord-28ec5cf8994d40ed92eab58e6f933e65
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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