Phosphorus oxychloride → HCID 14207943, compound

Temperature

110 °C

To 5-nitrothieno[2,3-b]pyridin-4-ol (607.9 mg, 3.099 mmol), POCl3 (6.00 mL) was added, then the mixture was stirred at 110° C. for 1 h. The reaction mixture was then concentrated under reduced pressure. The resulting residue was dissolved in DCM (50 mL), and a saturated aq. NaHCO3 (50 mL) was added slowly. The organic layer was washed with water (50 mL) and brine (50 mL), then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0 to 50% EtOAc in hexanes) to afford the sub-title compound as a pale yellow solid (605.3 mg, 91%). LCMS calc. for C7H4ClN2O2S (M+H)+: m/z=215.0. found 215.0.

1. concentrationThe reaction mixture was then concentrated under reduced pressure
2. dissolutionThe resulting residue was dissolved in DCM (50 mL)
3. additiona saturated aq. NaHCO3 (50 mL) was added slowly
4. washThe organic layer was washed with water (50 mL) and brine (50 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on silica gel (0 to 50% EtOAc in hexanes)

ORD record

ord-5a7981ee4b1340818223f3c2f16efaaf

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200004B2