4-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl [3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

HRID 425499Notes

Reaction equation

HRID 425499 reaction equation
BrC1C=CC=C2C=1C(C1C(O)=CC3OCOC=3C=1)[C:5](=[O:16])N2CCCCC.[OH:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][CH2:33][CH2:34]2)=[CH:30][C:29]=1[CH:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:39]([CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[C:38]1=[O:52]>>[OH:27][C:28]1[CH:36]=[C:35]2[C:31]([CH2:32][CH2:33][CH2:34]2)=[CH:30][C:29]=1[C:37]1([CH2:5][OH:16])[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:39]([CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])[C:38]1=[O:52]

Participants

3

Reactant 2

HCID 588725004-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 58872540ethyl [3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 58872532ethyl [3-(6-hydroxy-2,3-dihydro-1H-inden-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

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-2,3-dihydro-1H-inden-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained: MS (ES+) m/z 364 (M−17), 404 (M+23).

Sources & evidence

ORD record
ord-5e10b880ae994ffd86b181b38c4cc9fa
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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