4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 2-{3-[3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]propyl}-1H-isoindole-1,3(2H)-dione

HRID 425457Notes

Reaction equation

HRID 425457 reaction equation
BrC1C=CC=C2C=1C(O)(C1C(O)=CC3OCOC=3C=1)C(=O)N2CCCCC.O[C:29]1([C:53]2[C:61]([OH:62])=[CH:60][C:56]3[O:57][CH2:58][O:59][C:55]=3[CH:54]=2)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH2:38][CH2:39][CH2:40][N:41]2[C:49](=[O:50])[C:48]3[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:42]2=[O:51])[C:30]1=[O:52]>>[OH:62][C:61]1[C:53]([CH:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([CH2:38][CH2:39][CH2:40][N:41]3[C:49](=[O:50])[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[C:42]3=[O:51])[C:30]2=[O:52])=[CH:54][C:55]2[O:59][CH2:58][O:57][C:56]=2[CH:60]=1

Participants

3

Reactant 2

HCID 120044004-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588724962-{3-[3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]propyl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 588724372-{3-[3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]propyl}-1H-isoindole-1,3(2H)-dione

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 2-{3-[3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]propyl}-1H-isoindole-1,3(2H)-dione, the title compound was obtained (94%): 1H NMR (300 MHz, CDCl3,) δ 7.81-7.78 (m, 2H), 7.70-7.67 (m, 2H), 7.32-7.27 (m, 2H), 7.12-7.07 (m, 1H), 6.90-6.87 (m, 1H), 6.54 (s, 1H), 6.45 (s, 1H), 5.86 (dd, 2H), 4.82 (s, 1H), 3.96-3.66 (m, 4H), 2.17-2.04 (m, 2H); MS (ES+) m/z 457.0 (M+1).

Sources & evidence

ORD record
ord-c8e19a5151bf43de9dcb999cb16ccc00
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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