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), 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, dichloromethane (96 mg, 0.12 mmol) and 1,4-dioxane (30 mL). 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 then diluted with EtOAc (100 mL). The mixture was transferred to a separatory funnel and washed with water (50 mL×2). The combined aqueous phases were extracted with EtOAc (50 mL×2). The combined organic phases were dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified using column chromatography on silica gel (40 g RediSep column, gradient 30% EA in hexane to 100% EA in hexane) to give the product (420 mg; 77%) as a colorless crystalline solid: 1H NMR (400 MHz, CDCl3) δ 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