Reaktion #555832

Reaktionsgleichung

Cesium carbonate

3,5-difluoro-4-iodopyridin-2(1H)-one

ethyl (2R)-4-bromo-2-methyl-2-(methylsulfonyl)butanoate

→

title compound

Ausbeute 32.0%

Ethyl (2R)-4-(3,5-difluoro-4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanoate

Ausbeute 32.0%

Lösungsmittel

tetrahydrofuran t-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting suspension was heated
2. 2
   Temperaturto reflux
3. 3
   FiltrationThe reaction was filtered through celite
4. 4
   Waschenthe filter pad was washed with EtOAc (3×50 mL)
5. 5
   EinengenThe combined filtrates were concentrated
6. 6
   Sonstigethe crude product was purified via flash chromatography on an Analogix SF15-24 g column

Vorschrift

Cesium carbonate (1.90 g, 5.84 mmol) was added to a solution of the 3,5-difluoro-4-iodopyridin-2(1H)-one (1.0 g, 3.9 mmol) and ethyl (2R)-4-bromo-2-methyl-2-(methylsulfonyl)butanoate, T1, (1.45 g, 5.06 mmol) in tetrahydrofuran:t-butanol (1:1, 50 mL). The resulting suspension was heated to reflux and was stirred at this temperature for 72 h. The reaction was filtered through celite, and the filter pad was washed with EtOAc (3×50 mL). The combined filtrates were concentrated and the crude product was purified via flash chromatography on an Analogix SF15-24 g column using an eluent of EtOAc in hexanes (0-50%) to afford the title compound as a yellow solid (575.6 mg, 32%). MS (LCMS) m/z 463.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (s, 3H) 1.58 (s, 3H) 2.20 (dt, J=13.90, 7.00 Hz, 1H) 2.52-2.62 (m, 1H) 3.14 (s, 3H) 4.00 (t, J=7.61 Hz, 2H) 4.05-4.22 (m, 2H) 7.94 (dd, J=4.20, 2.05 Hz, 1H).

Quelle