Acetic Acid → 1-Methyl-1H-pyrazolo[3,4-B]pyridin-5-amine

HRID 1748320Notes

Reaction equation

HRID 1748320 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=[C:5]2[CH:4]=[N:3]1.C(O)(=O)C>C(Cl)Cl.[Zn]>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([NH2:11])[CH:10]=[C:5]2[CH:4]=[N:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 133713201-Methyl-5-nitro-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 552853851-Methyl-1H-pyrazolo[3,4-B]pyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1-methyl-5-nitro-1H-pyrazolo[3,4-b]pyridine (90 mg, 0.51 mmol) in CH2Cl2 (1 mL) is added zinc (200 mg, 3.06 mmol) and acetic acid (250 μL). The mixture is heated at 45° C. for 5 h. The zinc is removed by filtration and the filtrate was evaporated under reduced pressure. The residue is purified by flash column chromatography using a gradient of 0-10% methanol in CH2Cl2. 1N HCl in ether is added to the residue to afford the title compound as the hydrochloride salt (43 mg, 46%).

Workup

  1. customThe zinc is removed by filtration
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue is purified by flash column chromatography
  4. addition1N HCl in ether is added to the residue

Sources & evidence

ORD record
ord-cd6077561db042d19d0b6dbdc47afa63
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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