Sodium Hydroxide → 7-Chlorothieno[3,2-b]pyridine

Temperature

105 °C

A mixture of thieno[3,2-b]pyridin-7-ol (3.8 g, 25 mmol) and phosphorus oxychloride (18 g, 120 mmol) was stirred at 105° C. for 2 hr. The reaction mixture was added to ice water, and basified with 8N aqueous sodium hydroxide solution. Ethyl acetate was added, the insoluble material was filtered off, and the filtrate was extracted with ethyl acetate. The collected organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70), and the obtained solution was concentrated under reduced pressure to give the title compound (2.8 g, 66%) as a pale-yellow solid.

1. filtrationthe insoluble material was filtered off
2. extractionthe filtrate was extracted with ethyl acetate
3. washThe collected organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationthe insoluble material was filtered off
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)
8. concentrationthe obtained solution was concentrated under reduced pressure

ORD record

ord-bc714a952fb347148a7e54cd39ae3eb7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09090601B2