Ammonia → C-{3-(3-Fluoro-phenyl)-6-methoxy-1H-indazol-5-yl}-methylamine

HRID 503197Notes

Reaction equation

HRID 503197 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[F:11][C:12]1[CH:13]=[C:14]([C:18]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([C:27]#[N:28])[CH:25]=3)[NH:20][N:19]=2)[CH:15]=[CH:16][CH:17]=1.N>O1CCCC1>[F:11][C:12]1[CH:13]=[C:14]([C:18]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([CH2:27][NH2:28])[CH:25]=3)[NH:20][N:19]=2)[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 222607803-(3-Fluoro-phenyl)-6-methoxy-1H-indazole-5-carbonitrile

Product 1

HCID 22260835C-{3-(3-Fluoro-phenyl)-6-methoxy-1H-indazol-5-yl}-methylamineYield 212.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A total of 71 mg of lithium aluminium hydride was suspended in 4.7 ml of tetrahydrofuran, 249 mg of aluminium chloride was added under ice-cooling, and the mixture was stirred for 10 minutes. To the reaction mixture was added 50 mg of 3-(3-fluoro-phenyl)-6-methoxy-1H-indazole-5-carbonitrile obtained in Production Example II-1-d, followed by stirring at room temperature for 3 hours. The reaction mixture was ice-cooled, 27% aqueous ammonia was added and the mixture was filtrated through Celite. The filtrate was evaporated, and the residue was purified and separated by silica gel column chromatography (NH silica gel) (ethyl acetate), to give 108 mg of the title compound.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 3 hours
  3. temperaturecooled
  4. filtrationthe mixture was filtrated through Celite
  5. customThe filtrate was evaporated
  6. customthe residue was purified
  7. customseparated by silica gel column chromatography (NH silica gel) (ethyl acetate)

Sources & evidence

ORD record
ord-6396c920d037405abf97f72f70d3629e
Source dataset
uspto-grants-2010_08
Patent number
US07776890B2

Reaction notes

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