Azobisisobutyronitrile → HCID 178419527, compound

HRID 876760Notes

Reaction equation

HRID 876760 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 57370583Tert-butyl 3-methyl-1H-pyrazolo[3,4-B]pyridine-1-carboxylate

Product 1

HCID 178419527HCID 178419527, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of tert-butyl 3-methyl-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (B-4) (699 mg, 3 mmol) in CCl4 (15 mL) were added NBS (641 mg, 3.6 mmol) and AIBN (70 mg, 0.3 mmol). The reaction mixture was stirred under reflux overnight and then filtered. The filtrate was washed with saturated aqueous Na2CO3 (15 mL). The organic layer was dried over Na2SO4 and concentrated to afford the crude product. The crude product was used for next step without further purification. MS (m/z): 212 (M+1)+.

Workup

  1. temperatureunder reflux overnight
  2. filtrationfiltered
  3. washThe filtrate was washed with saturated aqueous Na2CO3 (15 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-25e74623de51463e9dea9d6b4ef8b85e
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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