3-(5-Fluoro-2-hydroxyphenyl)-1-pentylindolin-2-one → 3-(5-bromo-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 425481Notes

Reaction equation

HRID 425481 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:26]=[CH:27][C:28]([OH:46])=[C:29]([CH:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:32]2=[O:45])[CH:30]=1>>[Br:24][C:25]1[CH:26]=[CH:27][C:28]([OH:46])=[C:29]([C:31]2([CH2:9][OH:22])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[N:33]([CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:32]2=[O:45])[CH:30]=1

Participants

3

Reactant 2

HCID 588724603-(5-Fluoro-2-hydroxyphenyl)-1-pentylindolin-2-oneHCID 588725363-(5-bromo-2-hydroxyphenyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588724823-(5-bromo-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-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 3-(5-bromo-2-hydroxyphenyl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained: MS (ES+) m/z 386 (M−17), 388 (M−17), 426 (M+23), 428 (M+23).

Workup

  1. customas described in PREPARATION 14C

Sources & evidence

ORD record
ord-e1c73c8f254d47ca989cb8ecdb353c6f
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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