Electric Literature of 363-51-9,Some common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, molecular formula is C6H5ClFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 39: 1 -( r2-(Butyloxy)phenvnmethyl)-Lambda/-(2-chloro-6-fluorophenyl)-1 H- pyrazole-3-carboxamide.; To 1-{[2-(butyloxy)phenyl]methyl}-1 H-pyrazole-3-carboxylic acid (0.558 g, 2.03 mmol) was added thionyl chloride (5 ml, 68.5 mmol) followed by Lambda/,Lambda/-dimethylformamide (0.01 ml, 0.129 mmol). The reaction was stirred at ambient temperature under nitrogen for 22 h. The reaction mixture was concentrated in vacuo, then redissolved in DCM and re-concentrated (x 2) to give 1-{[2-(butyloxy)phenyl]methyl}-1 H-pyrazole- 3-carbonyl chloride as a very pale orange gum which solidified on standing (61 1 mg). To a solution of 2-chloro-6-fluoroaniline (29.1 mg, 0.2 mmol, Avacardo research Chemicals) in chloroform (0.2 ml) was added Lambda/,Lambda/-diisopropylethylamine (0.034 ml, 0.2 mmol) and dimethylaminopyridine (2 mg, 0.016 mmol). 1-{[2- (butyloxy)phenyl]methyl}-1 H-pyrazole-3-carbonyl chloride (29.2 mg, 0.1 mmol) in chloroform (0.2 ml) was then added and the resulting solution stirred and heated at 70 0C under reflux for 2 h. The solvent was removed under a stream of nitrogen and then dimethylsulphoxide (0.6 ml) added. The reaction mixture was purified by MDAP on SUNFIRE C18 column (Method D). The appropriate fraction was concentrated in vacuo then under nitrogen flow to give the title compound (9.8mg); LCMS: (System3) MH+= 402, tRET = 1.33 min.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-6-fluoroaniline, its application will become more common.
Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (2010); A1;,
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