HCID 68182358, compound → HCID 68182478, compound

HRID 524399Notes

Reaction equation

HRID 524399 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=2)[N:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:8]=[CH:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:11][CH:10]=2)[N:5]=1

Participants

4

Reactant 1

HCID 68182358HCID 68182358, compound

Product 1

HCID 68182478HCID 68182478, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 6-(3-nitropyrazol-1-yl)pyridine-3-carboxylate (0.505 gm, 1.74 mmol) in ethyl acetate (15 mL), 10% Pd/C (0.100 g, 20% w/w) was added under argon atmosphere. Argon gas was removed under vacuum and reaction flask was filled with hydrogen gas at 40 psi pressure. Reaction mixture was stirred for 1 hr on parr-apparatus. Reaction mixture was filtered through celite pad and concentrated under reduced pressure to give tert-butyl 6-(3-aminopyrazol-1-yl)pyridine-3-carboxylate (0.450 gm.)

Workup

  1. customArgon gas was removed under vacuum and reaction flask
  2. additionwas filled with hydrogen gas at 40 psi pressure
  3. customReaction mixture
  4. customReaction mixture
  5. filtrationwas filtered through celite pad
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff47926f7ba148448dc1743293eaf356
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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