Methyl iodide → 5-(2-Bromo-5-fluoro-phenyl)-1-methyl-2H-tetrazole

HRID 1788134Notes

Reaction equation

HRID 1788134 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[NH:13][N:12]=[N:11][N:10]=1.IC.[C:16](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:13]([CH3:16])[NH:12][NH:11][N:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505485HCID 178505485, compound

Product 1

HCID 210699275-(2-Bromo-5-fluoro-phenyl)-1-methyl-2H-tetrazoleYield 33%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(2-bromo-5-fluoro-phenyl)-1H-tetrazole (1.0 g, 4.12 mmol), iodomethane (1.12 g, 10 mmol) and potassium carbonate (1.5 g) in dimethylformamide (5 mL) was stirred at room temperature for 16 hrs, then concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2) to provide 350 mg (Yield 33%) of the title compound as white crystals. 1H NMR (500 MHz, CDCl3) o ppm: 4.00 (3 H, s) 7.18-7.25 (2 H, m) 7.72 (1 H, dd, J=8.4, 5.0 Hz); 13C NMR (126 MHz, CDCl3) δ ppm: 34.59, 117.73, 119.58, 120.43, 127.57, 135.11, 153.43, 161.69. LC/MS m/z 257/259.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-a773c69ff8624e18b0f51793686c325a
Source dataset
uspto-grants-2009_03
Patent number
US07511037B2

Reaction notes

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