Reaktion #478470

Reaktionsgleichung

2-chloro-4-(5-formylpyridin-3-yl)benzonitrile

2-Chloro-4-(5-formyl-pyridin-3-yl)-benzonitrile

ethanesulfonamide

Cyclopropylmagnesium bromide

→

N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was heated
2. 2
   Temperaturto reflux for 4 h
3. 3
   EinengenAfter concentration
4. 4
   workup.DISSOLUTIONthe residue was dissolved in THF (5 mL)
5. 5
   Temperaturthe resulting mixture was slowly warmed up to room temperature
6. 6
   SonstigeAfter quenching by saturated NH4Cl solution
7. 7
   Sonstigethe residue was purified by flash column (ethyl acetate-heptane, v/v, 40%-60%)
8. 8
   Sonstigeyielded a slightly yellow solid

Vorschrift

Titanium(IV) isopropoxide (0.365 mL, 1.245 mmol) was added to a mixture of 2-chloro-4-(5-formylpyridin-3-yl)benzonitrile (as prepared in Example 23, step 1; 0.151 g, 0.622 mmol), ethanesulfonamide (0.085 g, 0.778 mmol) in toluene (10 mL) at room temperature. The resulting mixture was heated to reflux for 4 h. After concentration, the residue was dissolved in THF (5 mL), and cooled to −40° C. Cyclopropylmagnesium bromide (3.73 mL, 1.867 mmol) was added dropwise, and the resulting mixture was slowly warmed up to room temperature and stirred overnight. After quenching by saturated NH4Cl solution, the residue was purified by flash column (ethyl acetate-heptane, v/v, 40%-60%) yielded a slightly yellow solid.

Quelle