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

HRID 1372240Notes

Reaction equation

HRID 1372240 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-30f19bc1ccb54114a4e2996e0c443df3
Source dataset
uspto-grants-2007_01
Patent number
US07157447B2

Reaction notes

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