Acetic Acid → 5-[6-(1-Hydroxy-1-methylethyl)pyridin-3-yl]-2-nitrothiophene-3-carboxamide

Temperatur

90 °C

To a solution of 5-[6-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)pyridin-3-yl]-2-nitrothiophene-3-carboxamide (665 mg, 1.58 mmol) in THF (10 mL) were added AcOH (0.36 ml, 6.13 mmol) and TBAF (1.0 M in THF, 6.31 mL, 6.31 mmol). The sealed reaction was stirred at 90° C. for 18 h. Additional AcOH (0.361 ml, 6.13 mmol) and TBAF (6.31 mL, 6.31 mmol) were added, and the reaction was stirred at 90° C. for another 24 h. The brown solution was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic extracts were washed with brine (2×), dried (MgSO4), filtered, and evaporated. Flash chromatography of the crude residue (50-100% EtOAc/hexanes) provided a yellow residue that was triturated with Et2O and filtered to isolate the title compound as a yellow solid.

1. customThe sealed reaction
2. stirringthe reaction was stirred at 90° C. for another 24 h
3. temperatureThe brown solution was cooled to room temperature
4. extractionextracted with EtOAc (2×)
5. washThe combined organic extracts were washed with brine (2×)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customFlash chromatography of the crude residue (50-100% EtOAc/hexanes) provided a yellow residue that
10. customwas triturated with Et2O
11. filtrationfiltered

ORD-Eintrag

ord-ec7bf98dcf244e28a98332a654b66ff2

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367706B2