Reaktion #605704

Reaktionsgleichung

N-[3-bromo-5-(2,4-difluorophenoxyl)phenyl]ethanesulfonamide

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

K3PO4

→

title compound

Ausbeute 94.0%

N-[3-(2,4-difluorophenoxy)-5-(1,5-dimethyl-6-oxopyridin-3-yl)phenyl]ethanesulfonamide

Ausbeute 94.0%

Lösungsmittel

dioxane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with nitrogen
2. 2
   Sonstigecapped
3. 3
   FiltrationAfter the mixture was filtered through a short bed of celite
4. 4
   Einengenthe filtrate was concentrated in vacuo
5. 5
   Sonstigepurified by silica gel column chromatography

Vorschrift

A mixture of N-[3-bromo-5-(2,4-difluorophenoxyl)phenyl]ethanesulfonamide (70 mg, 0.17 mmol), 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (44 mg, 0.18 mmol), Pd(dppf)Cl2 (12 mg) and K3PO4 (92 mg, 0.42 mmol) in dioxane (1 mL) and water (133 uL) was purged with nitrogen, capped, and heated to 75° C. for 1 h. After the mixture was filtered through a short bed of celite, the filtrate was concentrated in vacuo and purified by silica gel column chromatography using a gradient of MeOH (0 to 10%) in DCM to afford the title compound (69 mg, 94%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13-1.22 (m, 3H) 2.07 (s, 3H) 3.08-3.20 (m, 2H) 3.50 (s, 3H) 6.65-6.70 (m, 1H) 6.92-6.96 (m, 1H) 7.05-7.10 (m, 1H) 7.12-7.19 (m, 1H) 7.28-7.37 (m, 1H) 7.47-7.55 (m, 1H) 7.56-7.59 (m, 1H) 7.87-7.95 (m, 1H) 9.76-9.94 (m, 1H). LCMS (M+H)+=435.

Quelle