Hydrazine → 6-Chloro-1h-pyrazolo[3,4-b]pyridine

HRID 930572Notes

Reaction equation

HRID 930572 reaction equation
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][CH:5]=[C:4]([Cl:10])[N:3]=1.[NH2:11][NH2:12]>C1COCC1>[Cl:10][C:4]1[N:3]=[C:2]2[NH:11][N:12]=[CH:8][C:7]2=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 122593832,6-Dichloropyridine-3-carbaldehyde

Product 1

HCID 454802836-Chloro-1h-pyrazolo[3,4-b]pyridineYield 21.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloro-3-formylpyridine (0.89 mmol, 1 eq.) in 3 ml THF was added hydrazine (1.06 mmol, 1.2 eq.) at rt. The resultant solution was heated at 120° C. in sealed tube for overnight. The solvent was removed in vacuo, and the residue was dry loaded on silica gel column. Purification by silica gel chromatography provide 29.5 mg final product: HPLC retention time=2.17 minutes (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C.) using 1 ml/min flow rate, a 2.5 minute gradient of 0% to 100% B with a 1.1 minute wash at 100% B (A=0.1% formic acid/5% acetonitrile/94.9% water, B=0.1% formic acid/5% water/94.9% acetonitrile); MS (ES) M+H expect=154.0. found=154.0.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was dry
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-24daa3cf95c742ac89680e6e70d000dd
Source dataset
uspto-grants-2016_03
Patent number
US09296740B2

Reaction notes

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