Reaktion #46977

Reaktionsgleichung

19

1-(4-Methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-ylamine

isonicotinoyl chloride hydrochloride

cesium carbonate

→

compound 26

Ausbeute 82.0%

N-[1-(4-Methoxy-benzenesulfonyl)-2,3-dihydro-1H-indol-7-yl]-isonicotin amide

Ausbeute 82.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto reflux for 16 h
3. 3
   SonstigeThe reaction mixture was quenched with ice water
4. 4
   Extraktionextracted with CH2Cl2
5. 5
   TrocknenThe combined organic layer was dried over MgSO4
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto give a residue that
8. 8
   Sonstigewas purified by silica gel flash column chromatography (EtOAc:n-hexane :NH3(aq)=3:2:1%)
9. 9
   Sonstigerecrystallized (CH2Cl2/EtOAc)

Vorschrift

To a stirred mixture of 19 (0.2 g, 0.52 mmol), isonicotinoyl chloride hydrochloride (0.18 g, 1.04 mmol), and cesium carbonate (0.68 g, 2.08 mmol) in acetonitrile (20 ml) was heated to reflux for 16 h. The reaction mixture was quenched with ice water and extracted with CH2Cl2. The combined organic layer was dried over MgSO4 and evaporated to give a residue that was purified by silica gel flash column chromatography (EtOAc:n-hexane :NH3(aq)=3:2:1%) and recrystallized (CH2Cl2/EtOAc) to afford compound 26, yield 82%.

Quelle