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

HRID 1510102
Notes
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Reaction equation

HRID 1510102 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:22][C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[C:29]([F:32])[C:28]([OH:33])=[CH:27][CH:26]=2>CN(C1C=CN=CC=1)C.O1CCOCC1.CCOC(C)=O.O>[F:32][C:29]1[C:28]([O:33][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:27][CH:26]=[C:25]2[C:30]=1[CH:31]=[C:23]([CH3:22])[NH:24]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 103520364-fluoro-2-methyl-1H-indol-5-olHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

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

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent
HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-7-benzyloxy-6-methoxy-quinoline (WO2008112407, 1.5 g) was mixed with DMAP (1.5 eq), 2-methyl-4-fluoro-5-hydroxyindole (WO0047212) (1 eq) in dioxane (20 ml). The reaction was refluxed for three days and diluted with EtOAc, water and extracted with EtOAc three times. The combined organic layer was washed with water, brine and dried. The solution was evaporated and purified with silica gel column to give 4-(4-fluoro-2-methyl-1H-indol-5-yloxy)-6-methoxy-7-benzyloxyquinoline (600 mg).

Workup

  1. temperatureThe reaction was refluxed for three days
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layer was washed with water, brine
  4. customdried
  5. customThe solution was evaporated
  6. custompurified with silica gel column

Sources & evidence

ORD record
ord-19f0907e8cdb45f69fa35c78336f2dcb
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