Ammonium Chloride → C-{6-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1H-indazol-5-yl}-methylamine

HRID 34040Notes

Reaction equation

HRID 34040 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[F:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:17][NH:18]2)=[CH:14][C:13]=1[C:30]#[N:31].[Cl-].[NH4+]>O1CCCC1.C(OC(=O)C)C>[F:11][C:12]1[CH:20]=[C:19]2[C:15]([C:16](/[CH:21]=[CH:22]/[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:17][NH:18]2)=[CH:14][C:13]=1[CH2:30][NH2:31]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 59797063HCID 59797063, compound

Product 1

HCID 59797158C-{6-Fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1H-indazol-5-yl}-methylamineYield 32.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5 mg of lithium aluminum hydride in 1 mL of tetrahydrofuran was added 13 mg of aluminum chloride (III), followed by 9 mg of 6-fluoro-3-[(E)-2-(3-fluorophenyl)-vinyl]-1H-indazole-5-carbonitrile obtained by Example 100, and stirred at room temperature overnight. After adding saturated aqueous ammonium chloride, the reaction solution was added with 15 mL of ethylacetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate (twice) and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (methanol:chloroform=1:9), to afford 3 mg of the title compound as a yellow oil.

Workup

  1. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate (twice) and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was purified
  5. customseparated by silica gel column chromatography (methanol:chloroform=1:9)

Sources & evidence

ORD record
ord-cd58fe877cfc4d6dabc66232e71745f6
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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