Réaction #42101

Équation de réaction

MeMgBr

6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrile

product

2-chloro-6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carbonitrile

propionyl chloride

isobutyl amine

→

N-(6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutylpropionamide

Conditions de réaction

Traitement

1. 1
   AutreAfter 1 hour 45 minutes the reaction was quenched with 2 M aqueous HCl
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   Lavagewashed with saturated aqueous NaHCO3 solution
4. 4
   ConcentrationThe dried solution (Na2SO4) was concentrated
5. 5
   Autrepurified via flash chromatography on silica gel
6. 6
   Lavageeluted with 20% EtOAc in hexane affording the title compound

Mode opératoire

To 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrile [prepared by reacting the product of Example 1 step C with isobutyl amine] (0.26 g) in TH (2.5 mL) was added MeMgBr (0.47 mL, 1.4 M solution in toluene THF 3:1) followed by propionyl chloride. After 1 hour 45 minutes the reaction was quenched with 2 M aqueous HCl, diluted with EtOAc and washed with saturated aqueous NaHCO3 solution. The dried solution (Na2SO4) was concentrated and purified via flash chromatography on silica gel eluted with 20% EtOAc in hexane affording the title compound. HPLC/MS: 486.2(M+1), 488.2 (M+3); Rt=4.60 min.

Source