5-Bromo-2-ethylpyridine → 2-Ethyl-5-(1,2,3-triazol-2-yl)pyridine

HRID 850120Notes

Reaction equation

HRID 850120 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[N:11]1>>[CH2:8]([C:5]1[CH:4]=[CH:3][C:2]([N:11]2[N:12]=[CH:13][CH:14]=[N:10]2)=[CH:7][N:6]=1)[CH3:9]

Participants

3

Reactant 2

HCID 139797365-Bromo-2-ethylpyridineHCID 178418936HCID 178418936, compound

Product 1

HCID 193659842-Ethyl-5-(1,2,3-triazol-2-yl)pyridine

Procedure

The title compound was prepared from 5-bromo-2-ethylpyridine (Preparation 65) and 1,2,3-triazole by a similar method to Preparation 1. The regioisomeric product were separated by column chromatography on silica by gradient elution with ethyl acetate/hexane (1:1→1:0). Fractions containing the title compound eluted first, these were combined and evaporated under reduced pressure to yield an oil, which was distilled b.p.135° C. @ 0.05 mmHg (Kugelrohr).

Workup

  1. customThe regioisomeric product were separated by column chromatography on silica by gradient elution with ethyl acetate/hexane (1:1→1:0)
  2. additionFractions containing the title compound
  3. washeluted first
  4. customevaporated under reduced pressure
  5. customto yield an oil, which
  6. distillationwas distilled b.p.135° C. @ 0.05 mmHg (Kugelrohr)

Sources & evidence

ORD record
ord-988c10ea63c546018e894a8edfe7ec9c
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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