Reaktion #589439

Reaktionsgleichung

2-(4-aminophenyl)-1-cyclopropyl-6-(tetrahydrofuran-2-yloxy)indole-3-carbonitrile

1-cyclopropylethanol

→

{4-[3-cyano-1-cyclopropyl-6-(tetrahydrofuran-2-yloxy)indol-2-yl]phenyl}carbamic acid 1-cyclopropylethyl ester

Ausbeute 68.0%

Lösungsmittel

pyridine

water

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is then stirred at 60° C. overnight
2. 2
   WaschenThe organic is washed with water (3×5 mL), HCl (2N, 3×5 mL), saturated NaHCO3 (3×5 mL)
3. 3
   Sonstigechromatographed (silica gel, EtOAc/DCM, 0.5/9.5)

Vorschrift

A mixture of 2-(4-aminophenyl)-1-cyclopropyl-6-(tetrahydrofuran-2-yloxy)indole-3-carbonitrile (36 mg, 0.1 mmol), 4-nitrophenylchloroformate (50 mg, 0.25 mmol) in pyridine (2.0 mL) is stirred at 35° C. for 2 h, followed by the addition of 1-cyclopropylethanol (98 μL, 1.0 mmol). The mixture is then stirred at 60° C. overnight and diluted with water (10 mL) and DCM (5 mL). The organic is washed with water (3×5 mL), HCl (2N, 3×5 mL), saturated NaHCO3 (3×5 mL) and chromatographed (silica gel, EtOAc/DCM, 0.5/9.5) to provide the title compound, {4-[3-cyano-1-cyclopropyl-6-(tetrahydrofuran-2-yloxy)indol-2-yl]phenyl}carbamic acid 1-cyclopropylethyl ester (32 mg, 68%).

Quelle