Reaktion #85723

Reaktionsgleichung

(R)—N—((S)-1-(4-bromo-2,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide

sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxy-[1,1′-biphenyl]-3-sulfonate

(2-(trifluoromethyl)pyridin-4-yl)boronic acid

K2CO3

→

(R)—N—((S)-1-(2,5-difluoro-4-(2-(trifluoromethyl)pyridin-4-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide

Lösungsmittel

dioxane H2O

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was sealed
2. 2
   TemperaturThe reaction mixture was then cooled to room temperature
3. 3
   ExtraktionThe aqueous layer was then extracted with EtOAc (2×20 mL)
4. 4
   EinengenThe combined organic was then concentrated
5. 5
   SonstigeThe residue was purified by silica gel chromatography (50% heptane in EtOAc to 10% MeOH in EtOAc)
6. 6
   Sonstigeto give product

Vorschrift

To a solution of (R)—N—((S)-1-(4-bromo-2,5-difluorophenyl)ethyl)-2-methylpropane-2-sulfinamide (230 mg, 0.676 mmol) in dioxane/H2O (5 mL/1 mL) was added sodium 2′-(dicyclohexylphosphino)-2,6-dimethoxy-[1,1′-biphenyl]-3-sulfonate (34.7 mg, 0.068 mmol), (2-(trifluoromethyl)pyridin-4-yl)boronic acid (194 mg, 1.014 mmol), K2CO3 (234 mg, 1.690 mmol) followed by Pd2dba3 (31.0 mg, 0.034 mmol). The reaction mixture was sealed and heated to 110° C. and stirred for 2 hours. LCMS show complete conversion. The reaction mixture was then cooled to room temperature and diluted with EtOAc (20 mL) and water (10 mL). The aqueous layer was then extracted with EtOAc (2×20 mL). The combined organic was then concentrated. The residue was purified by silica gel chromatography (50% heptane in EtOAc to 10% MeOH in EtOAc) to give product. (0.25 g). LCMS (B) m/z 407.6 (M+H)+

Quelle