Reaktion #74514

Reaktionsgleichung

N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-4-(4-fluoro-2-iodophenoxy)benzenesulfonamide

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

sodium carbonate

→

title compound

N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-4-[4-fluoro-2-(1H-pyrazol-4-yl)phenoxy]benzenesulfonamide

Lösungsmittel

dimethylformamide water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried over sodium sulfate
4. 4
   Sonstigeevaporated in vacuo
5. 5
   Sonstigeto afford a brown oil
6. 6
   SonstigePurification by preparative HPLC

Vorschrift

N-(5-Chloro-1,3-thiazol-2-yl)-3-cyano-4-(4-fluoro-2-iodophenoxy)benzenesulfonamide (Preparation 240, 50 mg, 0.09 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (27 mg, 0.14 mmol) palladium (0) tetrakis(triphenylphosphine) (10 mg, 0.009 mmol) and sodium carbonate (30 mg, 0.28 mmol) were dissolved in dimethylformamide:water (2:1, 1.5 ml) and heated to 90° C. for 18 hours. The reaction was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was separated, dried over sodium sulfate and evaporated in vacuo to afford a brown oil. Purification by preparative HPLC afforded the title compound. Yield 12.5 mg 30%.

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