Dimethylformamide → HCID 70855547, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, sodium carbonate (33 mg, 0.3 mmol), palladium tetrakis(triphenylphosphine) (35 mg, 0.03 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (78 mg, 0.3 mmol) were added to a solution of methyl (3-bromo-4-methyl-benzo[b]thiophen-2-yl)-tert-butoxy-acetate (23i) (100 mg, 0.28 mmol) in a mixture of water (1 mL) and N,N(-dimethylformamide (3 mL). The mixture was heated at 100° C. for 1 hour. The mixture was then cooled at room temperature, concentrated in vacuo and water (30 mL) was added. The aqueous layer was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine (30 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired product (23j) as a white solid (65 mg, 0.15 mmol, 57%).

Provenance & Evidence