Cyanogen Bromide → 6-Trifluoromethyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylamine hydrobromide

HRID 217690Notes

Reaction equation

HRID 217690 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][NH2:10])=[N:7][CH:8]=1.[N:13]#[C:14][Br:15]>CCO.O>[BrH:15].[F:12][C:2]([F:1])([F:11])[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:14]([NH2:13])=[N:10][N:9]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 14776422-Hydrazinyl-5-(trifluoromethyl)pyridine

Product 1

HCID 669360456-Trifluoromethyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylamine hydrobromideYield 41.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

5-(Trifluoromethyl)pyrid-2-ylhydrazine (500 mg) was dissolved at RT in a mixture of EtOH/water (7.5/1.5 ml) while stirring. Thereafter, cyanogen bromide solution (314 mg dissolved in EtOH/water 0.75/0.15 ml) was slowly and cautiously added dropwise within 30 min. After stirring at RT for 3 h, the precipitate was filtered off with suction and dried under high vacuum (oil pump). 329 mg of 6-trifluoromethyl-[1,2,4]triazolo[4,3-a]pyridin-3-ylamine hydrobromide were obtained.

Workup

  1. additioncautiously added dropwise within 30 min
  2. stirringAfter stirring at RT for 3 h
  3. filtrationthe precipitate was filtered off with suction
  4. customdried under high vacuum (oil pump)

Sources & evidence

ORD record
ord-e1659ed92ecf4776a82641a8d39505a8
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Reaction notes

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