Reaktion #605675

Reaktionsgleichung

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(2-trimethylsilylethynyl)pyridin-2-one

N-[3-Bromo-4-(2,4-difluorophenoxyl)phenyl]ethanesulfonamide

K3PO4

→

title compound

Ausbeute 38.7%

N-[4-(2,4-difluorophenoxy)-3-[1-methyl-6-oxo-5-(2-trimethylsilylethynyl)pyridin-3-yl]phenyl]ethanesulfonamide

Ausbeute 38.7%

Lösungsmittel

dioxane

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter the mixture was concentrated
2. 2
   Sonstigethe residue was purified by column chromatography on silica gel (PE: EA=2:1)

Vorschrift

A mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(2-trimethylsilylethynyl)pyridin-2-one (200 mg, 0.6 mmol), N-[3-Bromo-4-(2,4-difluorophenoxyl)phenyl]ethanesulfonamide (197 mg, 0.5 mmol), Pd(dppf)Cl2 (37 mg, 0.05 mmol) and K3PO4 (267 mg, 1.26 mmol) in dioxane (6 mL) and H2O (0.6 mL) was stirred at 70° C. under an atmosphere of argon for 12 h. After the mixture was concentrated, the residue was purified by column chromatography on silica gel (PE: EA=2:1) to give the title compound (100 mg, 38%) as a yellow solid. 1H NMR (CDCl3, 400 MHz): δ 7.82 (d, J=2.4 Hz, 1H), 7.67 (d, J=2.4 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 7.16-7.12 (m, 1H), 6.99-6.91 (m, 2H), 6.87-6.83 (m, 1H), 6.78 (m, 1H), 6.65 (s, 1H), 3.61 (s, 3H), 3.14 (q, J=7.2 Hz, 2H), 1.42 (t, J=7.2 Hz, 3H), 024 (s, 9H). LCMS (M+H)+=517.

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