Water → 5-Bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridine

HRID 1160190Notes

Reaction equation

HRID 1160190 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=2)=[N:4][N:3]=[N:2]1.[OH-].[Na+].I[CH3:16].O>CN(C)C=O>[CH3:16][N:4]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=2)=[N:1][N:2]=[N:3]1.[CH3:16][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=2)=[N:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 234386835-Bromo-2-(2H-tetrazol-5-yl)pyridine

Product 2

HCID 234385675-Bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridineHCID 234386535-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.5 g of 2-(tetrazol-5-yl)-5-bromopyridine prepared in the Preparation example 6 was dissolved in 100 ml of dimethylformamide. And then 6.5 g of sodium hydroxide was added to the solution and 9.3 g of iodomethane was slowly added to the solution at the temperature of 0° C. The solution was stirred for 6 hours at room temperature, added with water, extracted with ethyl acetate. And then the organic layer was washed with brine, dehydrated, filtrated, concentrated in vacuo and purified by column chromatography to obtain 4 g of 2-(1-methyltetrazol-5-yl)-5-bromopyridine and 5 g of 2-(2-methyltetrazol-5-yl)-5-bromopyridine.

Workup

  1. additionwas slowly added to the solution at the temperature of 0° C
  2. extractionextracted with ethyl acetate
  3. washAnd then the organic layer was washed with brine
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-aaea77b13ac54978a10c79cf21c9720e
Source dataset
uspto-grants-2010_10
Patent number
US07816379B2

Reaction notes

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