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

HRID 2120108Notes

Reaction equation

HRID 2120108 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.I[CH3:14].[OH-].[K+]>CN(C)C=O>[CH3:14][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

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 234386835-Bromo-2-(2H-tetrazol-5-yl)pyridine

Product 1

HCID 234385675-Bromo-2-(1-methyl-1H-tetrazol-5-yl)pyridineYield 25.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5 ml of dimethylformamide was dissolved 400 mg of 2-(5-tetrazolyl)-5-bromopyridine and the solution was reacted with 502 mg of iodomethane in the presence of 300 mg of potassium hydroxide at room temperature for 1 hour with stirring. After completion of the reaction, a post-treatment similar to that of Preparation Example 3 was conducted to obtain 110 mg of 2-(1-methyl-5-tetrazolyl)-5-bromopyridine (thin layer chromatography eluting with a mixture of 1:4 ethyl acetate:hexane, Rf: 0.3) and 220 mg of 2-(2-methyl-5-tetrazolyl)-5-bromopyridine (thin layer chromatography eluting with a mixture of 1:4 ethyl acetate:hexane, Rf: 0.5).

Workup

  1. customAfter completion of the reaction
  2. customa post-treatment similar to that of Preparation Example 3

Sources & evidence

ORD record
ord-214a21cf4c9548b486a95f4e2783055d
Source dataset
uspto-grants-2004_02
Patent number
US06689779B2

Reaction notes

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