Hydrochloric Acid → HCID 67245646, compound

Temperature

-78 °C

To a cold (−78° C.) solution of thieno[2,3-c]pyridine (2.040 g, 15.09 mmol) in anhydrous THF (50 mL) was added n-butyllithium (6.64 mL, 16.60 mmol) dropwise. The reaction mixture was stirred for 60 minutes at −78° C. A solution of triisopropyl borate (4.16 mL, 18.11 mmol) was added and the reaction mixture was stirred for 30 minutes at −78° C. The solution was allowed to warm to room temperature over a 2 hour period. TLC showed the reaction was complete. Aqueous HCl (1N, 1000 mL) and DCM (500 mL) were added to the reaction mixture. The aqueous and organic layers were separated. The aqueous layer was concentrated to a volume of 500 mL and a solid precipitate was filtered and dried to give the title compound as off-white, needle-shaped crystals (2.4 g, 74%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.24 (s, 1H), 8.41 (d, J=4.80 Hz, 1H), 8.66 (d, J=6.32 Hz, 1H), 9.10 (br s, 2H), 9.72 (br s, 1H).

1. stirringthe reaction mixture was stirred for 30 minutes at −78° C
2. temperatureto warm to room temperature over a 2 hour period
3. customThe aqueous and organic layers were separated
4. concentrationThe aqueous layer was concentrated to a volume of 500 mL
5. filtrationa solid precipitate was filtered
6. customdried

ORD record

ord-d700f18cadf94cfb95326e1e4a6cb41a

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09056873B2