Trifluoroacetic acid → [3-(3-Fluorophenyl)-1H-5-indazolyl]methanamine

HRID 1983473

Reaction equation

HRID 1983473 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C(OC(C)(C)C)=O)[N:7]=[C:6]2[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:25][C:21]1[CH:20]=[C:19]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][NH2:1])[CH:4]=3)[NH:8][N:7]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 222606941h-Indazole-1-carboxylic acid,5-(aminomethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

Product 1

HCID 22260728[3-(3-Fluorophenyl)-1H-5-indazolyl]methanamineYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 300 mg of tert-butyl 5-(aminomethyl)-3-(3-fluorophenyl)-1H-1-indazolecarboxylate in 1 ml methylene chloride was added 2 ml of trifluoroacetic acid, and the mixture was stirred at room temperature for 6.5 hours. After removing the solvent by filtration, to the residue was added 20 ml of ethyl acetate. The mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution (×2) and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 188 mg of the title compound as yellow crystals.

Workup

  1. customAfter removing the solvent
  2. filtrationby filtration
  3. additionto the residue was added 20 ml of ethyl acetate
  4. washThe mixture was sequentially washed with saturated aqueous sodium hydrogencarbonate solution (×2) and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-623963d954384d128b466199a06003b7
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Linked notes

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