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

HRID 645049Notes

Reaction equation

HRID 645049 reaction equation
BrC1C=CC=C2C=1C(C1C(O)=CC3OCOC=3C=1)[C:5](=[O:16])N2CCCCC.[CH2:27]([O:29][C:30](=[O:52])[CH2:31][N:32]1[C:40]2[C:35](=[C:36]([Br:41])[CH:37]=[CH:38][CH:39]=2)[CH:34]([C:42]2[CH:47]=[C:46]([F:48])[C:45]([F:49])=[CH:44][C:43]=2[OH:50])[C:33]1=[O:51])[CH3:28]>>[CH2:27]([O:29][C:30](=[O:52])[CH2:31][N:32]1[C:40]2[C:35](=[C:36]([Br:41])[CH:37]=[CH:38][CH:39]=2)[C:34]([C:42]2[CH:47]=[C:46]([F:48])[C:45]([F:49])=[CH:44][C:43]=2[OH:50])([CH2:5][OH:16])[C:33]1=[O:51])[CH3:28]

Participants

3

Reactant 2

HCID 588725004-bromo-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 58872550ethyl [4-bromo-3-(4,5-difluoro-2-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 58872533ethyl [4-bromo-3-(4,5-difluoro-2-hydroxyphenyl)-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[4-bromo-3-(4,5-difluoro-2-hydroxyphenyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained (83%): MS (ES+) m/z 456.3 (M+1), 458.3 (M+1).

Sources & evidence

ORD record
ord-92f2e47de39d428b9303213af52c4b6f
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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