HCID 58119006, compound → HCID 39080128, compound

HRID 406433Notes

Reaction equation

HRID 406433 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-])=O)[C:5]2[N:6]([C:8]([CH:11]([CH3:13])[CH3:12])=[N:9][N:10]=2)[CH:7]=1>C(O)(=O)C.CO.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5]2[N:6]([C:8]([CH:11]([CH3:12])[CH3:13])=[N:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 1

HCID 58119006HCID 58119006, compound

Product 1

HCID 39080128HCID 39080128, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Compound B was prepared by heating A, 6-bromo-3-isopropyl-8-nitro-[1,2,4]triazolo[4,3-a]pyridine, prepared as described in Example 9A, Step 1, (0.777 mmole) in acetic acid (6 mL) in the presence of Zinc dust (3.89 mmole) at 60 C for 1 hour. The reaction mixture was then diluted with methanol and filtered to celite. The filtrate was concentrated down and the residue was then filtered through silica gel with first ethyl acetate and then with 1:4 mixture of methanol and dichloromethane. The filtrate was evaporated in vacuo to yield B, 6-bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-8-amine.

Workup

  1. customprepared
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated down
  4. filtrationthe residue was then filtered through silica gel with first ethyl acetate
  5. additionwith 1:4 mixture of methanol and dichloromethane
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-d687fd6820544f06ac0d61e2aa58819e
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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