4-bromo-3-hydroxy-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)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate
Reaction equation
BrC1C=CC=C2C=1C(O)(C1C(O)=CC3OCOC=3C=1)C(=O)N2CCCCC.[CH2:28]([O:30][C:31](=[O:54])[CH2:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35](O)([C:42]2[C:50]([OH:51])=[CH:49][C:45]3[O:46][CH2:47][O:48][C:44]=3[CH:43]=2)[C:34]1=[O:53])[CH3:29]>>[CH2:28]([O:30][C:31](=[O:54])[CH2:32][N:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]([C:42]2[C:50]([OH:51])=[CH:49][C:45]3[O:46][CH2:47][O:48][C:44]=3[CH:43]=2)[C:34]1=[O:53])[CH3:29]Participants
3
Reactant 2
Product 1
Procedure
Following the procedure as described in PREPARATION 1D, and making non-critical variations to replace 4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with ethyl[3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained (84%) as a white powder: 1H NMR (300 MHz, DMSO-d6) δ 9.37 (s, 1H), 7.19 (m, 1H), 7.01-6.90 (m, 3H), 6.43 (s, 2H), 5.84 (m, 2H), 4.86 (s, 1H), 4.56 (s, 2H), 4.13 (q, 2H), 1.18 (t, 3H); MS (ES+) m/z 378.2 (M+23).
Sources & evidence
- ORD record
- ord-d744ebb81aca40f08d3d50a443741386
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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