Acetic Acid → HCID 72207298, compound

A mixture of 5,7-dichlorothieno[2,3-c]pyridine (1.86 g, 8.20 mmol), AcOH (9.42 mL, 164 mmol), and concentrated HCl (3.16 mL, 38.4 mmol) was treated with tin powder (3.04 g, 24.6 mmol) at 60° C. After 3 h heating, another portion of concentrated HCl (3.16 mL) was added followed by another portion of tin powder (3.04 g). After 2 h heating, another portion of concentrated HCl (3.16 mL) was added followed by tin powder (1.03 g). After 2 h, the heating was stopped, and the reaction mixture was cooled and diluted with water (50 mL). After filtration, the residue was washed with water. The combined filtrates were extracted with EtOAc (4×100 mL). The combined extracts were washed with aqueous 1 N NaOH until the pH was >9, followed by brine (100 mL), dried over MgSO4, and concentrated in vacuo. Purification by ISCO chromatography (0 to 30% EtOAc:heptane) afforded 980 mg (70%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.93 (d, J=0.4 Hz, 1 H), 7.79 (d, J=6.4 Hz, 1 H), 7.75 (d, J=1.2 Hz, 1 H), 7.33 (dd, J=5.6, 0.8 Hz, 1 H); MS (ESI): 169.98, 171.98 [M+H]+; HPLC tR=1.29 min (TOF: polar—3 min).

1. temperatureAfter 3 h heating
2. temperatureAfter 2 h heating
3. temperaturethe reaction mixture was cooled
4. filtrationAfter filtration
5. washthe residue was washed with water
6. extractionThe combined filtrates were extracted with EtOAc (4×100 mL)
7. washThe combined extracts were washed with aqueous 1 N NaOH until the pH was >9
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. customPurification by ISCO chromatography (0 to 30% EtOAc:heptane)

ORD record

ord-3070a21f60b24326bef569b5ac76f3af

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2