Ammonium Chloride → 6-Fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-1-trityl-1H-indazol-5-ylamine

HRID 34039Notes

Reaction equation

HRID 34039 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](/[CH:30]=[CH:31]/[C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)=[N:7][N:8]2[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N+:39]([O-])=O.[Cl-].[NH4+]>CN(C)C=O.[Fe]>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](/[CH:30]=[CH:31]/[C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)=[N:7][N:8]2[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][C:3]=1[NH2:39]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 689284926-Fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-5-nitro-1-trityl-1H-indazole

Product 1

HCID 689324356-Fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-1-trityl-1H-indazol-5-ylamineYield 92%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 290 mg of 6-fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-5-nitro-1-trityl-1H-indazole in a mixture of 5 mL N,N-dimethylformamide/9 mL methanol/1 mL water were added 30 mg of ammonium chloride and 150 mg of iron powder, and stirred at 80° C. for 8 hours. After filtering off the insoluble substances through Celite, the solvent was evaporated, and the resultant residue was dissolved in 15 mL of ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated, to afford 252 mg of the title compound as pale brown non-crystalline powder.

Workup

  1. filtrationAfter filtering off the insoluble substances through Celite
  2. customthe solvent was evaporated
  3. dissolutionthe resultant residue was dissolved in 15 mL of ethyl acetate
  4. washThe organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a73ce881fdf9422392bc852c4dd6979d
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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