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

HRID 1752948Notes

Reaction equation

HRID 1752948 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 sodiumhydroxide 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-90a8cdac34d84cf7a1e1d95ef04f57fa
Source dataset
uspto-grants-2015_10
Patent number
US09163043B2

Reaction notes

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