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

HRID 645070Notes

Reaction equation

HRID 645070 reaction equation
BrC1C=CC=C2C=1C(C1C(O)=CC3OCOC=3C=1)[C:5](=[O:16])N2CCCCC.[CH2:27]([O:29][C:30](=[O:53])[CH2:31][N:32]1[C:40]2[C:35](=[C:36]([Cl:41])[CH:37]=[CH:38][CH:39]=2)[CH:34]([C:42]2[C:43]([OH:51])=[CH:44][C:45]3[O:49][CH2:48][CH2:47][C:46]=3[CH:50]=2)[C:33]1=[O:52])[CH3:28]>>[CH2:27]([O:29][C:30](=[O:53])[CH2:31][N:32]1[C:40]2[C:35](=[C:36]([Cl:41])[CH:37]=[CH:38][CH:39]=2)[C:34]([C:42]2[C:43]([OH:51])=[CH:44][C:45]3[O:49][CH2:48][CH2:47][C:46]=3[CH:50]=2)([CH2:5][OH:16])[C:33]1=[O:52])[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 58872564ethyl [4-chloro-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 58872569ethyl [4-chloro-3-(6-hydroxy-2,3-dihydro-1-benzofuran-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[4-chloro-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 (99%) as a gummy solid: MS (ES+) m/z 418.7 (M+1).

Sources & evidence

ORD record
ord-23070ba85be44ef6bf2833a3f8ddcf2e
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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