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With n-butyllithium; carbon dioxide; In petroleum; di-isopropyl ether; water;
Reference Example 9 A solution of <strong>[138006-41-4]3-bromo-2,5-dichloropyridine</strong> (10g) in diisopropyl ether was added dropwise to a stirred solution of n-butyllithium (2.5 M in hexanes, 17.7ml) in diisopropyl ether at -70oC under an inert atmosphere so that the reaction temperature did not exceed -68oC. An excess of solid carbon dioxide was then added to the suspension and the mixture was stirred for 2 hours (excess carbon dioxide evaporates, temperature reaches 10oC.). Ice/water was added, the mixture was stirred. The layers were separated. The aqueous layer was acidified to pH 2 with concentrated hydrochloric acid. The resulting precipitate was extracted into diethyl ether. The ether extracts were washed with water, dried (magnesium sulphate) and evaporated to yield a solid which was triturated in light petroleum to yield 2,5-dichloronicotinic acid as a cream solid (7.04g), m.p. 160-162oC.
2,5-dichloro-N-(3-methylsulfonylphenyl)pyridine-3-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
83.4%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In chloroform; at 20℃; for 22h;
A mixture of HBTU (217 mg, 0.571 mmol), DIPEA (200 pL, 1.15 mmol), 2,5-dichloropyridine-3-carboxylic acid (100 mg, 0.521 mmol) and 3- methylsulfonylaniline (93.6 mg, 0.547 mmol) in chloroform (5 mL) was stirred at room temperature for 22 h. The contents were treated with 5% Na2C03 and extracted with CHC13 (3x). The solvent was removed in vacuo to give 2,5-dichloro-N-(3- methylsulfonylphenyl)pyridine-3-carboxamide (150 mg, 0.435 mmol, 83.4% yield) as a semi-solid which was used without further purification. MS, ES+m/z 344.8[M+H]+.
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