Reaktion #1712848

Reaktionsgleichung

5-Bromo-2-ethoxypyridine

potassium carbonate

[2′-[(tert-butoxycarbonyl-ethyl-amino)-methyl]-6-methoxy-4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-yl]-acetic acid ethyl ester

→

title compound

[2′-[(tert-Butoxycarbonyl-ethyl-amino)-methyl]-4′-(6-ethoxy-pyridin-3-yl)-6-methoxy-biphenyl-3-yl]-acetic acid ethyl ester

Lösungsmittel

ethyl acetate

water

DME

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was purged with nitrogen
2. 2
   Temperaturthe mixture was cooled to room temperature
3. 3
   SonstigeThe aqueous layer was separated
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Trocknenthe combined organic layers were dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by silica gel chromatography (0-40% ethyl acetate in hexanes)

Vorschrift

5-Bromo-2-ethoxypyridine (0.235 g, 1.16 mmol), [2′-[(tert-butoxycarbonyl-ethyl-amino)-methyl]-6-methoxy-4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-yl]-acetic acid ethyl ester (0.500 g, 0.903 mmol), and potassium carbonate (0.313 g, 2.3 mmol) were combined in DME (5 mL) and water (2.5 mL) under nitrogen. The mixture was purged with nitrogen, and then tetrakis(triphenylphosphine)palladium(0) (0.052 g, 0.045 mmol) was added, and the reaction was heated to 85° C. for 6 hours. Once no starting material was seen by analytical LCMS, the mixture was cooled to room temperature and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate, and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography (0-40% ethyl acetate in hexanes) to give the title compound.

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