6-(4-nitro-1H-pyrazol-1-yl)isoquinoline → 1-(isoquinolin-6-yl)-1H-pyrazol-4-amine

HRID 598876Notes

Reaction equation

HRID 598876 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[N:14][CH:13]=[CH:12]3)[CH:8]=1)([O-])=O>[Pd].C1COCC1>[CH:15]1[C:16]2[C:11](=[CH:10][C:9]([N:7]3[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]3)=[CH:18][CH:17]=2)[CH:12]=[CH:13][N:14]=1

Participants

4

Reactant 1

HCID 670626806-(4-nitro-1H-pyrazol-1-yl)isoquinoline

Product 1

HCID 670626421-(isoquinolin-6-yl)-1H-pyrazol-4-amineYield 82.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-(4-nitro-1H-pyrazol-1-yl)isoquinoline (367 mg, 1.53 mmol) and 10 wt. % palladium on activated carbon (163 mg, 153 μmol) in THF (15 mL) was stirred under an atmosphere of hydrogen at ambient temperature for 4 hours. The mixture was filtered through a Celite pad that was washed with THF (30 mL), and the combined filtrates were concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, evaporated onto silica gel, and purified by flash chromatography (Biotage Si 40+M, 3% to 8% MeOH/DCM) to provide 1-(isoquinolin-6-yl)-1H-pyrazol-4-amine (264 mg, 82% yield) as a yellow solid. LCMS (API-ES) m/z (%): 211.2 (100%, M++H); 1H NMR (300 MHz, CDCl3) δ ppm 3.01 (br s, 2H), 7.48 (s, 1H), 7.62-7.69 (m, 2H), 7.93 (s, 1H), 7.96-8.06 (m, 2H), 8.52 (d, J=5.8 Hz, 1H), 9.22 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through a Celite pad that
  2. washwas washed with THF (30 mL)
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. dissolutionThe resulting yellow solid was dissolved in MeOH/DCM
  5. customevaporated onto silica gel
  6. custompurified by flash chromatography (Biotage Si 40+M, 3% to 8% MeOH/DCM)

Sources & evidence

ORD record
ord-e9476eaeea0746539bafc13a95d27cea
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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