Potassium Carbonate → (S)-3-bromo-7-(2-fluoropyridin-3-yl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

関与物質

反応条件

反応手順

A pressure reaction vessel was charged with (S)-3-bromo-7-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (1.512 g, 3.19 mmol, prepared as described in Method BB26), potassium carbonate (2.20 g, 15.95 mmol), 2-fluoropyridin-3-ylboronic acid (0.72 g, 5.10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.37 g, 0.32 mmol), dioxane (21.26 mL) and water (10.63 mL). The reaction was stirred and heated at 100° C. for 1 h. After cooling for rt, the reaction was diluted with water (25 mL) and poured into a separatory funnel containing ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with EtOAc (1×100 mL). The combined organic layers were washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo to provide a brown foam that was purified by silica gel chromatography (Redi-Sep pre-packed silica gel column (40 g), 0-100% EtOAc in 90/10 CH2Cl2:CH3OH to provide a white solid, (S)-3-bromo-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (0.65 g, 1.47 mmol, 46.0% yield). MS m/z=443.0 [M+H]+. Calc'd for C19H12BrFN4OS: 441.99.

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