تفاعل #75468

ord-f7f961427d9648d283d0fa156689af53

معادلة التفاعل

Cn1cc(C(=O)O)c(C(F)(F)F)c1
1-methyl-4-trifluoromethylpyrrole-3-carboxylic acid
O=C(Cl)C(=O)Cl
oxalyl chloride
Nc1cnccc1-c1ccc(Cl)cc1
3-amino4-(4′-chlorophenyl)pyridine
CCN(CC)CC
triethylamine
Cn1cc(C(=O)Nc2cnccc2-c2ccc(Cl)cc2)c(C(F)(F)F)c1
1-Methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic Acid [4-(4-Chlorophenyl)-pyridin-3-yl]amide

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    غسيلthe organic phase is washed twice with water
  2. 2
    تجفيفAfter drying the organic phase over sodium sulfate
  3. 3
    أخرىthe solvent is removed in a water
  4. 4
    أخرىThe obtained crude product
  5. 5
    أخرىis purified by column chromatography over silica gel (eluant: hexane/THF 1:3)

الإجراء التجريبي

A solution of 0.54 g (2.8 mmol) 1-methyl-4-trifluoromethylpyrrole-3-carboxylic acid and 0.39 g (3.1 mmol) oxalyl chloride in 20 ml methylene chloride is stirred for 2 hours at room temperature in the presence of a catalytic amount of DMF. Then the acid chloride solution is slowly added to a solution of 0.57 g (2.8 mmol) 3-amino4-(4′-chlorophenyl)pyridine, 0.34 g (3.4 mmol) triethylamine and 15 ml methylene chloride. The resulting mixture is then stirred for 16 hours at room temperature. After the addition of ethylacetate, the organic phase is washed twice with water. After drying the organic phase over sodium sulfate, the solvent is removed in a water let vacuum. The obtained crude product is purified by column chromatography over silica gel (eluant: hexane/THF 1:3). Yield: 0.4 g 1-methyl-4-trifluoromethyl-1-1-pyrrole-3-carboxylic acid [4-(4′-chlorophenyl)pyridin-3yl]amide in the form of yellowish crystals; m.p.: 178-180° C.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06699818B1uspto-grants-2004_03