Reaktion #1984961

Reaktionsgleichung

NH4Cl

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

ethanesulfonamide

toluene

→

title compound

Ausbeute 30.0%

N-((5-(4-cyano-3-fluorophenyl)pyridin-3-yl)(cyclopropyl)-methyl)ethanesulfonamide

Ausbeute 30.0%

Lösungsmittel

ethyl acetate

brine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was heated
2. 2
   Temperaturto reflux for 2 h
3. 3
   EinengenAfter concentration
4. 4
   workup.DISSOLUTIONthe residue was dissolved in THF (10 mL)
5. 5
   Filtrationsubsequently filtered
6. 6
   SonstigeThe organic layer was separated
7. 7
   Einengento concentrate
8. 8
   Sonstigepurified by flash column (10% MeOH/DCM=0-30%)

Vorschrift

Titanium isopropoxide (0.98 mL, 3.36 mmol) was added to a mixture of 2-fluoro-4-(5-formyl-pyridin-3-yl)-benzonitrile (380 mg, 1.68 mmol) and ethanesulfonamide (183 mg, 1.68 mmol) in toluene (14 mL) at RT. The resulting mixture was heated to reflux for 2 h. After concentration, the residue was dissolved in THF (10 mL) and a solution of c-PrMgBr (0.5 M in THF, 16.8 mL, 8.40 mmol) was added dropwise at −40° C., and the resulting mixture was stirred at −36° C. for 1 h. Saturated NH4Cl solution was added to the reaction mixture. The resulting mixture was diluted with ethyl acetate and brine, and subsequently filtered. The organic layer was separated to concentrate and purified by flash column (10% MeOH/DCM=0-30%) to give the title compound (185 mg, 30%); ESI-MS m/z: 360 [M+1]+, 1HNMR (MeOD, 400 MHz) δ ppm 8.85 (1H, d, J=2.0 Hz), 8.72 (1H, d, J=2.0 Hz), 8.25 (1H, t, J=2.0 Hz), 7.94 (1H, d, J=8.0 Hz), 7.82-7.77 (2H, m), 3.95 (1H, d, J=9.2 Hz), 3.89 (3H, s), 3.07-2.96 (2H, m), 1.34-1.29 (1H, m), 1.31 (1H, t, J=7.2 Hz), 0.81-0.76 (1H, m), 0.67-0.62 (2H, m), 0.55-0.51 (1H, m)

Quelle