Dimethylformamide → 3-Fluoro-4-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Temperatur

90 °C

A 15 mL sealed tube was charged with 7-chloro-2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridine (0.113 g, 0.449 mmol), 4-amino-2-fluorophenol (0.071 g, 0.56 mmol), cesium carbonate (0.512 g, 1.57 mmol), and DMF (2.00 ml) and sealed. The reaction mixture was stirred at 90° C. for 18 hours, allowed to cool to room temperature, then diluted with chloroform (50 mL) and washed with water (50 mL), sat. aq. NaHCO3 (50 mL), and brine (50 mL). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to yield a black solid. The product was purified by silica gel chromatography eluting with 3% methanol in methylene chloride to yield 3-fluoro-4-(2-(3-methyl-1,2,4-oxadiazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine (0.074 g, 48% yield) as a yellow solid.

1. customA 15 mL sealed tube
2. customsealed
3. temperatureto cool to room temperature
4. washwashed with water (50 mL), sat. aq. NaHCO3 (50 mL), and brine (50 mL)
5. dry with materialThe organic layer was dried with MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto yield a black solid
9. customThe product was purified by silica gel chromatography
10. washeluting with 3% methanol in methylene chloride

ORD-Eintrag

ord-f02fb9a135e6458689051e73607bfe61

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08685983B2