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

Temperature

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 record

ord-a4d6829cfab24caf9ccbd924e8da02f2

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088794B2