Hydrochloric Acid → HCID 67979568, compound

Participants

Reaction Steps

n-BuLi (2.5 M in hexanes, 5.46 mL, 13.7 mmol) was added dropwise to a solution of 3-bromo-5-(but-1-ynyl)pyridine (Intermediate 48, 2.39 g, 11.4 mmol) and triisopropyl borate (3.15 mL, 13.65 mmol) in 2-Me THF (20 mL) at −50° C. The mixture was stirred for 1.5 h while the temperature was kept between −50 and −40° C. The mixture was lifted up from the cooling bath and 2 M aq. HCl (12 mL, 24 mmol) was added followed by stirring for 20 min. The mixture was diluted with EtOAc. Aq. NaOH (2 M) was added until pH about 12 was obtained in the aqueous phase. The phases were separated. The organic phase was extracted with dilute aq. NaOH and with water. The combined aqueous phases were washed with EtOAc, acidified to pH about 5 by the addition of conc. HCl and extracted with DCM. The organic phase was dried over Na2SO4 and concentrated to give 1.522 g (76% yield) of the title compound: 1H NMR (500 MHz, CDCl3) δ ppm 1.11-1.37 (m, 3 H), 2.26-2.58 (m, 2 H), 7.46-10.34 (m, 3 H); MS (ES+) m/z 176 [M+H]+.

Provenance & Evidence