Hydrochloric Acid → N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamine

HRID 244402Notes

Reaction equation

HRID 244402 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH:11]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2)[C:12]([F:15])([F:14])[F:13])([O-])=O.Cl.C(=O)(O)[O-].[Na+]>CO.[Zn]>[F:15][C:12]([F:13])([F:14])[CH:11]([NH:10][C:5]1[C:4]([NH2:1])=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)[N:20]=[CH:19]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59437215(2-Nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine

Product 1

HCID 24960191N-{2,2,2-Trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}benzene-1,2-diamineYield 14%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of 100 mg (0.23 mmol) of (2-nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine in 10 mL of methanol was added 304 mg (4.65 mmol) of zinc powder followed by the addition of 4.65 mL (4.65 mmol) of 1 N aqueous HCl. After 1 hour, the mixture was made basic with saturated aqueous sodium bicarbonate and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by prep-TLC using 10-20% EtOAc/hexanes to provide 10 mg (14%) of the title compound as a white solid. MS m/z 401 (MH+).

Workup

  1. extractionextracted with three 15 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-643e4eecb17d4f46ab63ae14627652fd
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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