Hexane → HCID 66761094, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 3-bromo-5-methoxythieno[2,3-c]pyridine (14.7 mg, 0.0602 mmol) in THF (2.5 mL) was added dropwise 1.60 M n-BuLi in hexane (56.4 μL, 0.0903 mmol) in 5 min under an atmosphere of nitrogen. After stirring at −78° C. for 1 h, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (18.8 μL, 0.0903 mmol) was added dropwise. The combined mixture was stirred at −78° C. for another 1 h. The temperature was then gradually raised to RT in 40 min. The reaction was then quenched by addition of MeOH (5 mL) and purified by ISCO chromatography (0 to 20% EtOAc:hexane) to afford 6.6 mg (38%) of the title compound as a light yellow solid. 1H NMR (400 MHz, dioxane-d8): δ 8.72 (d, J=1.2 Hz, 1 H), 8.29 (s, 1 H), 7.48 (d, J=0.8 Hz, 1 H), 3.93 (s, 3 H), 1.35 (s, 12 H); MS (ESI): 292.11 [M+H]+; HPLC tR=1.71 min (TOF: polar—3 min).

Provenance & Evidence