Cyanogen Bromide → 7-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-amine

HRID 643669Notes

Reaction equation

HRID 643669 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][NH2:9])[CH:3]=1.[N:10]#[C:11]Br>CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:11]([NH2:10])=[N:9][N:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen Bromide2×HCID 534028634-Bromo-2-hydrazinylpyridine

Product 1

HCID 533932737-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 1-(4-bromopyridin-2-yl)hydrazine (0.710 g, 3.78 mmol) in 10 mL of 2-propanol was added cyanogen bromide (0.400 g, 3.78 mmol) at 25° C. The reaction was heated at 70° C. for 2 h and the reaction was monitored by LCMS. Additional cyanogen bromide (0.060 g) was added and the reaction was continued for another 2 h. The reaction was filtered while hot and the solid was washed with 2-propanol and pentane, and dried in vacuo to give the title compounds as a light orange amorphous solid. MS m/z: 214.9 [M+1].

Workup

  1. filtrationThe reaction was filtered while hot and the solid
  2. washwas washed with 2-propanol and pentane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-98f3346704474eb1b91179205fe480f6
Source dataset
uspto-grants-2010_04
Patent number
US07700593B2

Reaction notes

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