Réaction #67328

Équation de réaction

2-[2-(4′-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1H-indole-6-carboxylic acid methyl ester

intermediate 15-2

bromoethylacetate

NaH

→

2-[2-(4′-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1-methoxycarbonylmethyl-1H-indole-6-carboxylic acid methyl ester

Rendement 39.3%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.WAITAfter 24 h
2. 2
   FiltrationThe formed yellow solid was filtered off
3. 3
   Lavagewashed with petroleum ether
4. 4
   Autrepurified by column chromatography (CH2Cl2)

Mode opératoire

To a mixture of intermediate 15-2 (1.024 g, 1.7 mmol) and bromoethylacetate (388 mg, 1.5 eq) in dry DMF (30 mL) was added NaH (60% dispersion in mineral oil, 122 mg, 1.8 eq) at 0° C. After stirring for 20 min at this temperature, the reaction mixture was warmed up to room temperature. After 24 h, the reaction mixture was poured into 300 mL of ice-cold water. The formed yellow solid was filtered off, washed with petroleum ether and purified by column chromatography (CH2Cl2) to give 450 mg (39%) of 2-[2-(4′-Chloro-4-methoxy-biphenyl-2-yl)-quinolin-6-yl]-3-cyclohexyl-1-methoxycarbonylmethyl-1H-indole-6-carboxylic acid methyl ester 15-3; m/z=674 (M+H+).

Source