Ethyl Acetate → HCID 67499549, compound

HRID 2408179Notes

Reaction equation

HRID 2408179 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([CH3:16])=[N:9]2)[CH:7]=1.C(OCC)(=O)C>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:12]=[C:11]([NH2:13])[C:10]([CH3:16])=[N:9]2)[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67499514HCID 67499514, compound

Product 1

HCID 67499549HCID 67499549, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-fluoro-5-(3-methyl-4-nitro-1H-pyrazol-1-yl)pyridine (3.133 g, 14.10 mmol) in ethanol (28.2 ml) was added ethyl acetate until all of the starting material went into solution. The solution was degassed and 10% palladium on carbon (0.750 g, 0.705 mmol) was added and the reaction was stirred in a parr hydrogenator at 40 psi for 3 hours. The solution was filtered through celite with ethyl acetate and concentrated to give 1-(5-fluoropyridin-3-yl)-3-methyl-1H-pyrazol-4-amine (2.000 g, 10.41 mmol, 73.8%) as a brown solid: mp 136.0-138.0° C.; 1H NMR (400 MHz, CDCl3) δ 8.67-8.59 (m, 1H), 8.27 (d, J=2.5 Hz, 1H), 7.73 (dt, J=9.9, 2.3 Hz, 1H), 7.45 (s, 1H), 3.01 (s, 2H), 2.28 (s, 3H); EIMS m/z 192.

Workup

  1. customThe solution was degassed
  2. filtrationThe solution was filtered through celite with ethyl acetate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-16c77292cb654b5ba8ccbf4d8f810d0d
Source dataset
uspto-grants-2014_08
Patent number
US08815271B2

Reaction notes

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