Benzo(B)Thiophene-2-Boronic Acid → HCID 46228238, compound

Participants

Reaction Conditions

Reaction Steps

Compound 2 (5.0 g, 29.1 mmol), benzo[b]thiophene-2-ylboronic acid (6.23 g, 35.0 mmol), and tetrakis-(triphenylphosphine) palladium(0) (1.07 g, 0.87 mmol) were added to an RBF equipped with a reflux condenser and dissolved in a mixed solvent system of toluene (150 mL) and ethanol (50 mL). After addition of 50 mL of aqueous 2 N sodium carbonate solution, the reaction mixture was heated at 80° C. for 2 days. The organic phase was separated and extracted with methylene chloride. The organics were then combined, dried over Na2SO4 and filtered. The solvent was evaporated to give the crude product. The resulting crude product was then purified by silica gel column chromatography (eluent: ethyl acetate:methylene chloride=1:30 v/v) to yield 6.12 g (78%) of methyl 6-(benzo[b]thiophen-2-yl)nicotinate (Compound 3).

Provenance & Evidence