5-(2-Bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole → 4-Fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrile

HRID 1788132Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:10]=[N:11][N:12]([CH3:14])[N:13]=1.[C:15]([Cu])#[N:16]>CN(C)C=O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]#[N:16])=[C:3]([C:9]2[N:10]=[N:11][N:12]([CH3:14])[N:13]=2)[CH:4]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of intermediate 57, 5-(2-bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole (650 mg, 2.53 mmol) and CuCN (224 mg, 2.5 mmol) in dimethylformamide (4 mL) was placed in a sealed tube and heated at 100-110° C. for 20 hrs. After cooling, the insoluble material was filtered, and the filtrate concentrated in vacuo. The residue was dissolved in CH2Cl2, washed with aq. 4N HCl and dil. NH4OH, then dried (MgSO4), filtered, and concentrated. The residual solid was purified by column chromatography (SiO2, CH2Cl2) to obtain 375 mg (Yield 73%) of the title compound as an off-white solid; 1H NMR (500 MHz, CDCl3) δ ppm: 4.48 (3 H, s) 7.29 (1 H, dd, J=7.6, 2.8 Hz) 7.85 (1 H, dd, J=8.6, 5.2 Hz) 8.00 (1 H, dd, J=9.0, 2.6 Hz); LC/MS m/z 204.

Workup

customwas placed in a sealed tube
temperatureAfter cooling
filtrationthe insoluble material was filtered
concentrationthe filtrate concentrated in vacuo
dissolutionThe residue was dissolved in CH2Cl2
washwashed with aq. 4N HCl and dil. NH4OH
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe residual solid was purified by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record: ord-8f797b4d64954af09da982c4095dd489
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07511037B2

Reaction notes

Loading…