Reaction #75468

Reaction equation

1-methyl-4-trifluoromethylpyrrole-3-carboxylic acid

oxalyl chloride

3-amino4-(4′-chlorophenyl)pyridine

triethylamine

→

1-Methyl-4-trifluoromethyl-1H-pyrrole-3-carboxylic Acid [4-(4-Chlorophenyl)-pyridin-3-yl]amide

Solvents

ethylacetate

methylene chloride

DMF

methylene chloride

Conditions

Workup

1. 1
   Washthe organic phase is washed twice with water
2. 2
   DryingAfter drying the organic phase over sodium sulfate
3. 3
   Otherthe solvent is removed in a water
4. 4
   OtherThe obtained crude product
5. 5
   Otheris purified by column chromatography over silica gel (eluant: hexane/THF 1:3)

Procedure

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.

Source