HCID 90021306, compound → 5-Bromo[1,2,3]triazolo[1,5-a]pyridine

HRID 1487893Notes

Reaction equation

HRID 1487893 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](/[CH:8]=[N:9]/[NH:10]S(C2C=CC(C)=CC=2)(=O)=O)[CH:3]=1>N1CCOCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:10]=[N:9][CH:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 1

HCID 90021306HCID 90021306, compound2×

Product 1

HCID 159399545-Bromo[1,2,3]triazolo[1,5-a]pyridineYield 99.1%

Reagents, catalysts & solvents 2

HCID 8083MorpholineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-N′-((4-bromopyridin-2-yl)methylene)-4-methylbenzenesulfonohydrazide (compound 40.1, 3.8 g, 10.7 mmol) in morpholine (12 mL) was heated at 130° C. for 3 hours. The reaction mixture was cooled to room temperature, then diluted with EtOAc (150 mL) and washed with water (2×30 mL). The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes:EtOAc 4:1) to yield 2.10 g (99%) of the title compound as a light yellow solid. m/z (ES+) 198, 200 (M+H)+.

Workup

  1. washwashed with water (2×30 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexanes:EtOAc 4:1)

Sources & evidence

ORD record
ord-622e5c04f95145048c76738fdd75a830
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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