Reaktion #171169

Reaktionsgleichung

sodium bicarbonate

5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine]

triethylamine

2-chloro-isonicotinoyl chloride

→

1-(2-chloropyridin-4-yl)carbonyl-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine]

Ausbeute 49.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   Trocknendried (Na2SO4)
3. 3
   Einengenconcentrated in vacuo

Vorschrift

A solution of 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (150 mg) and triethylamine (0.24 ml) in dichloromethane (5 ml) at 0° C. under argon was treated with 2-chloro-isonicotinoyl chloride (147 mg). The resulting solution was stirred at room temperature for 1 hour, poured into saturated aqueous sodium bicarbonate, extracted with ethyl acetate, dried (Na2SO4) and concentrated in vacuo. Silica gel chromatography of the residue (eluent cyclohexane:ethyl acetate 6:4) afforded the title compound, 1-(2-chloropyridin-4-yl)carbonyl-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (95 mg), which was characterised by its mass and NMR spectra. MS (ES+) 498/500 (M+H+).

Quelle