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

HRID 545669Notes

Reaction equation

HRID 545669 reaction equation
BrC1C=CC=C2C=1C(O)(C1C(O)=CC3OCOC=3C=1)C(=O)N2CCCCC.O[C:29]1([C:45]2[C:53]([OH:54])=[CH:52][C:48]3[O:49][CH2:50][O:51][C:47]=3[CH:46]=2)[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:30]1=[O:44]>>[OH:54][C:53]1[C:45]([CH:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:31]([CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:30]2=[O:44])=[CH:46][C:47]2[O:51][CH2:50][O:49][C:48]=2[CH:52]=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 58872476ethyl [3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 58872556ethyl [3-(6-hydroxy-1,3-benzodioxol-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

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-e5ccbb2164824bf1bc19c3fdde409e67
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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