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4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline → HCID 136029933, compound

HRID 1510104
Notes
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Reaction equation

HRID 1510104 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24]CC4C=CC=CC=4)=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:32])[NH:6]2>[Pd]>[F:1][C:2]1[C:10]([O:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:24])=[C:19]([O:22][CH3:23])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:32])[NH:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 592007474-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline

Product 1

HCID 136029933HCID 136029933, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-(4-Fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline (600 mg) was mixed with HCONH4 (600 mg) and Pd/C (10%, 100 mg) followed by refluxing 30 min. The reaction was filtered while it was hot and the filtrate was evaporated and washed with water followed by filtration to give 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-hydroxyquinoline (400 mg).

Workup

  1. temperature
by refluxing 30 min
  • filtrationThe reaction was filtered while it
  • customthe filtrate was evaporated
  • washwashed with water
  • filtrationfollowed by filtration
  • Sources & evidence

    ORD record
    ord-6c1a8a71c276453f8465a3665428d815
    Source dataset
    uspto-grants-2012_07
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08211911B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes