Sodium Nitrite → 5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1774951Notes

Reaction equation

HRID 1774951 reaction equation
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:3]=1.[N:15]([O-])=O.[Na+]>CC(O)=O>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:4]2[CH:3]=[C:2]3[CH:1]=[N:15][NH:8][C:7]3=[CH:6][N:5]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 463152564-Methyl-6-(pyridin-3-yl)pyridin-3-amine

Product 1

HCID 866766805-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-methyl-2,3′-bipyridin-5-amine (185 g, 1 mol) in AcOH (27 L) was added aq. NaNO2 solution (82 g, 1.2 mol, 100 mL). The mixture was stirred for 16 h at room temperature. After reaction, the solvent was removed and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to give 5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine as a yellow solid (98 g, 50%)

Workup

  1. customAfter reaction
  2. customthe solvent was removed
  3. customthe residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1)

Sources & evidence

ORD record
ord-69d41fa444684570bfc16effe06db8f2
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…