Stannous Chloride → 1H-Pyrazolo[3,4-b]pyridin-5-amine

HRID 1038029Notes

Reaction equation

HRID 1038029 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.Cl[Sn]Cl>CCO.CC1C=CC=CC=1>[NH:10]1[C:7]2=[N:8][CH:9]=[C:4]([NH2:1])[CH:5]=[C:6]2[CH:12]=[N:11]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 123527765-nitro-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 461929221H-Pyrazolo[3,4-b]pyridin-5-amine

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Conditions

Temperature
70 °C

Procedure

5-Nitro-1H-pyrazolo[3,4-b]pyridine (prepared according to the procedure in Can. J. Chem. 1988, 66(3), 420) (133 mg, 0.81 mmol) was mixed with SnCl2 (1.09) in EtOH/CH3Ph (4 mL/2 mL) and heated at 70° C. for 3 hrs. The reaction was cooled to rt and concentrated to dryness. The residue was participated between 1.0 N NaOH (10 mL) and ethyl acetate (50 mL). The organic layer was washed with brine once, dried (MgSO4) and filtered. The filtrate was concentrated and the resulting crude was purified by prep. TLC using 10:2 CH2Cl2/Methanol (2 N NH3). The title compound (15.0 mg) was isolated as a yellow solid.

Workup

  1. temperatureThe reaction was cooled to rt
  2. concentrationconcentrated to dryness
  3. washThe organic layer was washed with brine once
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe resulting crude was purified by prep

Sources & evidence

ORD record
ord-eee63e62607a40cb93b7406dba4674c8
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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