Reaktion #1493587

Reaktionsgleichung

intermediate ( 5d )

5-Iodo-2-methyl-6-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

5-iodo-methyl-6-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

potassium carbonate

1-(tert-butoxycarbonyl) indole-2-boronic acid

dichloromethane

→

title compound

2-Methyl-5-(1-methyl-1H-indol-2-yl)-6-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

Lösungsmittel

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe contents of the vial were degassed
2. 2
   TemperaturAfter cooling
3. 3
   Sonstigethe reaction mixture was partitioned between brine (50 mL) and ethyl acetate (50 mL)
4. 4
   SonstigeThe organic layer was separated
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe resultant crude product was purified by flash chromatography on SiO2 with hexane—15% ethyl acetate/hexane (gradient)

Vorschrift

A microwave vial (20 mL) was charged with intermediate (5d), 5-iodo-methyl-6-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (0.87 g, 1.99 mmol), potassium carbonate (0.825 g, 5.97 mmol), 1-(tert-butoxycarbonyl) indole-2-boronic acid (0.624 g, 2.39 mmol), [1,1′-Bis(diphenylphosphino)ferrocene)]dichloropalladium(II), complex with dichloromethane (0.082 g, 5 mol %), tetrahydrofuran (14 mL) and water (2.3 mL). The contents of the vial were degassed and then heated at 60° C. for 1 hour under microwave irradiation. After cooling, the reaction mixture was partitioned between brine (50 mL) and ethyl acetate (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The resultant crude product was purified by flash chromatography on SiO2 with hexane—15% ethyl acetate/hexane (gradient) to afford the title compound as a yellow foam, 1.02 g, 97%.

Quelle