Reaktion #605670

Reaktionsgleichung

4-bromo-2,6-dimethylfuro[2,3-c]pyridin-7-one

N-[4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide

K3PO4

→

title compound

Ausbeute 12.0%

N-[4-(2,4-difluorophenoxy)-3-(2,6-dimethyl-7-oxofuro[2,3-c]pyridin-4-yl)phenyl]ethanesulfonamide

Ausbeute 12.0%

Lösungsmittel

dioxane water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas bubbled with argon for 5 min
2. 2
   TemperaturAfter cooling to rt
3. 3
   workup.ADDITIONthe reaction mixture was poured into water (10 mL)
4. 4
   Extraktionextracted with EtOAc (40 mL×3)
5. 5
   WaschenThe combined organic layers were washed with brine (20 mL×2)
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe residue was purified by prep-HPLC

Vorschrift

A mixture of 4-bromo-2,6-dimethylfuro[2,3-c]pyridin-7-one (200 mg, 0.83 mol), N-[4-(2,4-difluorophenoxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanesulfonamide (364 mg, 0.99 mmol), Pd(dppf)Cl2 (66 mg, 0.09 mmol), K3PO4 (527 mg, 2.49 mmol) in dioxane/water (4 mL/1 mL) was bubbled with argon for 5 min. The mixture was heated to 70° C. for 18 h. After cooling to rt, the reaction mixture was poured into water (10 mL) and extracted with EtOAc (40 mL×3). The combined organic layers were washed with brine (20 mL×2), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by prep-HPLC to afford the title compound (49 mg, 12%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ 7.35-7.33 (m, 2H) 7.12 (m, 1H) 6.95-6.89 (m, 2H) 6.81 (m, 2H) 6.43 (s, 1H) 6.38 (s, 1H) 3.71 (s, 3H) 3.16 (q, J=7.2 Hz, 2H) 2.47 (s, 3H) 1.43 (t, J=7.2 Hz, 3H). LCMS (M+H)+=475.

Quelle