2-Methyl-2H-pyrazol-3-ylamine → 1-Methyl-5-nitro-1H-pyrazolo[3,4-b]pyridine

HRID 1748319Notes

Reaction equation

HRID 1748319 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][CH:4]=[N:3]1.[Na].[N+:9]([CH:12]([CH:15]=O)[CH:13]=O)([O-:11])=[O:10]>C(O)(=O)C>[CH3:1][N:2]1[C:6]2=[N:7][CH:13]=[C:12]([N+:9]([O-:11])=[O:10])[CH:15]=[C:5]2[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 24193465CID 24193465

Product 1

HCID 133713201-Methyl-5-nitro-1H-pyrazolo[3,4-b]pyridineYield 19%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
108 °C

Procedure

To a solution of 1-methyl-1H-pyrazol-5-amine (291 mg, 3.00 mmol) in acetic acid (3 mL) is added nitromalonaldehyde sodium salt (474 mg, 3.00 mmol) and reaction mixture is heated to 108° C. for 1 h. The reaction mixture is allowed to cool to room temperature and is stirred for 16 h. The solvent is evaporated under reduced pressure and the residue is purified by flash column chromatography using a gradient of 0-100% ethyl acetate in heptane to afford the title compound as a solid (100 mg, 19%).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-df71cc400ba145d191d78db69136b8a4
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…