HCID 67235215, compound → HCID 28373930, compound

HRID 1521744Notes

Reaction equation

HRID 1521744 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:8]=1)([O-])=O>CO.[Pd]>[N:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 67235215HCID 67235215, compound

Product 1

HCID 28373930HCID 28373930, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-[(4-nitro-1H-pyrazol-1-yl)methyl]pyridine (247 mg, 1.21 mmol) in methanol (10 mL) is hydrogenated over 10% palladium on carbon (30 mg) under balloon pressure for 3 h. The mixture is filtered through Celite® and the filtrate is concentrated under reduced pressure. The residue is purified via flash column chromatography using a gradient elution of 0-10% CH2Cl2/methanol to afford the title compound as a brown oil (198 mg, 94%).

Workup

  1. filtrationThe mixture is filtered through Celite®
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue is purified via flash column chromatography
  4. washa gradient elution of 0-10% CH2Cl2/methanol

Sources & evidence

ORD record
ord-b02b4eb8a7f9487e88545ec927385f89
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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