Isobutyryl chloride → 6-Bromo-3-(propan-2-yl)[1,2,4]triazolo[4,3-a]pyridine--hydrogen chloride (1/1)

HRID 1822752Notes

Reaction equation

HRID 1822752 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.[C:10]([Cl:15])(=O)[CH:11]([CH3:13])[CH3:12]>CCCCCC>[ClH:15].[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH:11]([CH3:13])[CH3:12])=[N:9][N:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 62325Isobutyryl chlorideHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 221701776-Bromo-3-(propan-2-yl)[1,2,4]triazolo[4,3-a]pyridine--hydrogen chloride (1/1)

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 500 ml three-necked round-bottomed flask equipped with a mechanical stirrer and a condenser, connected on top to a nitrogen bubbler and a thermometer, was charged with 5-bromo-pyridin-2-yl-hydrazine (43.4 g, 0.231 moles) and isobutyryl chloride (218 ml, 2.08 moles). The mixture was gently refluxed for 3 hours. The heating source was then replaced with an ice-water bath and the slurry cooled to room temperature. Hexane (220 ml) was added and the slurry stirred at room temperature for 15 minutes and filtered. The cake was washed with hexane (3×70 ml) and then dried in a vacuum-oven (35° C.) for 48 hours. The title compound was obtained as an off-white powder (58.96 g, yield 92.3%).

Workup

  1. customA 500 ml three-necked round-bottomed flask equipped with a mechanical stirrer and a condenser
  2. temperatureThe mixture was gently refluxed for 3 hours
  3. customThe heating source was then replaced with an ice-water bath
  4. filtrationfiltered
  5. washThe cake was washed with hexane (3×70 ml)
  6. customdried in a vacuum-oven (35° C.) for 48 hours

Sources & evidence

ORD record
ord-5c4d89b59354498790c3175fc79acb2d
Source dataset
uspto-grants-2006_05
Patent number
US07037923B2

Reaction notes

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