4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl [5-chloro-3-(6-hydroxy-2,3-dihydro-1-benzofuran-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:55])[CH2:32][N:33]1[C:41]2[C:36](=[CH:37][C:38]([Cl:42])=[CH:39][CH:40]=2)[C:35](O)([C:43]2[C:44]([OH:52])=[CH:45][C:46]3[O:50][CH2:49][CH2:48][C:47]=3[CH:51]=2)[C:34]1=[O:54])[CH3:29]>>[CH2:28]([O:30][C:31](=[O:55])[CH2:32][N:33]1[C:41]2[C:36](=[CH:37][C:38]([Cl:42])=[CH:39][CH:40]=2)[CH:35]([C:43]2[C:44]([OH:52])=[CH:45][C:46]3[O:50][CH2:49][CH2:48][C:47]=3[CH:51]=2)[C:34]1=[O:54])[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[5-chloro-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained (94%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.30-7.24 (m, 2H), 6.72 (d, 1H), 6.66 (s, 1H), 6.39 (s, 1H), 5.05 (s, 1H), 4.53-4.46 (m, 4H), 4.21 (q, 2H), 3.14-2.94 (m, 2H), 1.25 (t, 3H); MS (ES+) m/z 388.8 (M+1).
Sources & evidence
- ORD record
- ord-f16bb614c6704372a148575f51286a65
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700641B2
Reaction notes
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