Ammonium formate → HCID 178507358, compound

HRID 1038009Notes

Reaction equation

HRID 1038009 reaction equation
C([O-])=O.[NH4+].[F:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=2)[NH:11][N:10]=1>CO.C1COCC1.CO.[Pd]>[F:5][C:6]1[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=1[CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=2)[NH:11][N:10]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 178526492HCID 178526492, compound

Product 1

HCID 178507358HCID 178507358, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Ammonium formate (50 mg, 0.792 mmol) and 10% Pd/C (5 mg) were added to a solution of 3-(2-fluoro-benzyl)-5-nitro-1H-indazole (50 mg, 0.184 mmol) in MeOH/THF (3 ml, 1/1) then refluxed for 3 hours. The reaction was diluted with MeOH (20 ml) and filtered through a celite pad. The solvent was evaporated, residue dissolved in MeCl2, dried over Na2SO4, filtered and solvent evaporated yielding title compound as white solid (40 mg, 88%) ESMS (MH, 242).

Workup

  1. temperaturethen refluxed for 3 hours
  2. filtrationfiltered through a celite pad
  3. customThe solvent was evaporated
  4. dissolutionresidue dissolved in MeCl2
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-691d3d532ecb4f0d91e5b5a6deafdc92
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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