4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one → 4-Bromo-3-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-3-(hydroxymethyl)indolin-2-one

HRID 425578Notes

Reaction equation

HRID 425578 reaction equation
FC1C=CC(O)=C(C2C3C(=CC=CC=3)N(CCCCC)[C:9]2=[O:22])C=1.[Br:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH:27]([C:35]1[C:36]([OH:44])=[CH:37][C:38]3[O:42][CH2:41][CH2:40][C:39]=3[CH:43]=1)[C:28](=[O:34])[NH:29]2>>[Br:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[C:27]([C:35]1[C:36]([OH:44])=[CH:37][C:38]3[O:42][CH2:41][CH2:40][C:39]=3[CH:43]=1)([CH2:9][OH:22])[C:28](=[O:34])[NH:29]2

Participants

3

Reactant 2

HCID 120044054-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-oneHCID 588724603-(5-Fluoro-2-hydroxyphenyl)-1-pentylindolin-2-one

Product 1

HCID 588724384-Bromo-3-(6-hydroxy-2,3-dihydrobenzofuran-5-yl)-3-(hydroxymethyl)indolin-2-one

Procedure

Following the procedure as described in PREPARATION 14C, and making non-critical variations to replace 3-(5-fluoro-2-hydroxyphenyl)-1-pentyl-1,3-dihydro-2H-indol-2-one with 4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained (16%): Rf=0.21 (EtOAc/Hexanes, 7/3).

Workup

  1. customas described in PREPARATION 14C

Sources & evidence

ORD record
ord-276c274c3daa472e9bceb0be364d4418
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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