Reaktion #589432

Reaktionsgleichung

α-methylcyclopropane methanol

2-(4-aminophenyl)-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indole-3-carbonitrile

pyridine

4-nitrophenyl chloroformate

→

title compound

[4-(3-cyano-1-cyclobutyl-6-(2-methoxyethoxy)-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester

Lösungsmittel

1,1 dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is heated to 70° C. for 5 h
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigethe reaction is partitioned between ethyl acetate (10 mL) and saturated K2CO3 (10 mL)
4. 4
   WaschenThe organic phase is washed with additional saturated K2CO3 (2×10 mL), water, and saturated NaCl
5. 5
   TrocknenThe colorless solution is dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   WaschenThe remaining solid is washed with diethyl ether

Vorschrift

To a solution of 2-(4-aminophenyl)-1-cyclobutyl-6-(2-methoxy-ethoxy)-1H-indole-3-carbonitrile (76.0 mg, 0.21 mmol), pyridine (36.5 mg, 0.46 mmol) in 10 mL of 1,1 dichloroethane is added 4-nitrophenyl chloroformate (93.2 mg, 0.46 mmol). The resulting mixture is stirred at room temperature for 2 h. Then α-methylcyclopropane methanol (54.3 mg, 0.63 mmol) is added. The reaction mixture is heated to 70° C. for 5 h. After cooling, the reaction is partitioned between ethyl acetate (10 mL) and saturated K2CO3 (10 mL). The organic phase is washed with additional saturated K2CO3 (2×10 mL), water, and saturated NaCl. The colorless solution is dried over MgSO4, filtered and evaporated. The remaining solid is washed with diethyl ether to yield the title compound, of [4-(3-cyano-1-cyclobutyl-6-(2-methoxyethoxy)-1H-indol-2-yl)-phenyl]-carbamic acid 1-cyclopropyl-ethyl ester (compound 1423) as a white solid.

Quelle