Potassium Carbonate → 2-bromo-6-(2H-1,2,3-triazol-2-ylmethyl)pyridine

HRID 386050

Reaction equation

HRID 386050 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[N:11]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:10]2[CH:14]=[CH:13][N:12]=[N:11]2)[N:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:11]2[N:12]=[CH:13][CH:14]=[N:10]2)[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 178418936HCID 178418936, compound

Product 2

HCID 595259132-bromo-6-(2H-1,2,3-triazol-2-ylmethyl)pyridineHCID 595262962-bromo-6-(1H-1,2,3-triazol-1-ylmethyl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (1.50 g, 5.98 mmol), 1H-1,2,3-triazole (520 mL, 8.97 mmol), and K2CO3 (1.652 g, 11.96 mmol) were combined in DMF (5.0 mL) and stirred at 50° C. overnight. The mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (0-100% EtOAc/hexanes) separated the two regioisomeric products to provide 2-bromo-6-(1H-1,2,3-triazol-1-ylmethyl)pyridine (lower Rf) and 2-bromo-6-(2H-1,2,3-triazol-2-ylmethyl)pyridine (higher Rf) as colorless solids.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customFlash chromatography (0-100% EtOAc/hexanes) separated the two regioisomeric products

Sources & evidence

ORD record
ord-505833c16d4d489597ec0678d217be8e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

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