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

HRID 348135Notes

Reaction equation

HRID 348135 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) δ ppm: 4.00 (3H, s) 7.18–7.25 (2H, m) 7.72 (1H, 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-aab5c96b148d453f8751356c2d42465c
Source dataset
uspto-grants-2007_02
Patent number
US07176196B2

Reaction notes

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