Dichloromethane → HCID 68183135, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 ml round bottomed flask, were placed 2-bromo-5,5-dimethyl-6,7-dihydro-1-benzothiophen-4(5H)-one (550 mg, 2.1 mmol), pyridine-4-boronic acid (326 mg, 2.65 mmol) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (96 mg, 0.12 mmol) and then suspended in 1,4-dioxane (30 mL, 400 mmol). To the mixture were added cesium carbonate (3.08 g, 9.45 mmol) and water (20 mL). The mixture was stirred for 16 h at 120° C. The mixture was allowed to cool to rt and then diluted with EtOAc (100 mL), which was washed with water (50 mL×2). The combined aqueous phase was extracted with EtOAc (50 mL×2). The combined organic phase was dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (40 g) column chromatography eluted with a 30% to 100% EtOAc/hexane to obtain title compound (420 mg, 77%) as a colorless crystalline solid. LCMS: (FA) ES+ 258; 1H NMR (400 MHz, d-chloroform) δ ppm 8.60 (dd, 2H), 7.77 (s, 1H), 7.43 (dd, 2H), 3.09 (t, 2H), 2.10 (t, 2H), 1.24 (s, 6H).

Provenance & Evidence