Reaktion #663476

Reaktionsgleichung

mixture

7-bromo-1-(4-methoxybenzyl)-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carbonitrile

o-tolylboronic acid

CsF

→

1-(4-methoxybenzyl)-3-(3-(naphthalen-1-yloxy)propyl)-7-o-tolyl-1H-indole-2-carbonitrile

Lösungsmittel

1,2-dimethoxyethane

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under nitrogen for 4 hours
2. 2
   EinengenThe mixture was concentrated under vacuum
3. 3
   Sonstigethe residue was partitioned between ethyl acetate (300 mL) and water (100 ml)
4. 4
   ExtraktionThe aqueous layer was further extracted with ethyl acetate
5. 5
   Waschenthe combined extracts were washed with water, brine
6. 6
   Trocknendried over Na2SO4
7. 7
   FiltrationAfter filtration, concentration of the solvent and column purification (5 to 10% ethyl acetate in hexane)
8. 8
   Sonstigegave EXAMPLE 581D

Vorschrift

To a mixture of EXAMPLE 581C (300 mg) and o-tolylboronic acid (93 mg) in 1,2-dimethoxyethane (10 ml) and methanol (5 ml) was added tetrakis(triphenylphosphine)palladium(0) (33 mg) and CsF (260 mg). The mixture was stirred at reflux under nitrogen for 4 hours. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (300 mL) and water (100 ml). The aqueous layer was further extracted with ethyl acetate and the combined extracts were washed with water, brine and dried over Na2SO4. After filtration, concentration of the solvent and column purification (5 to 10% ethyl acetate in hexane) gave EXAMPLE 581D.

Quelle