(4-chloro-2-ethoxycarbonylphenyl)boronic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of [4-chloro-2-(ethoxycarbonyl)phenyl]boronic acid (3-1, 0.300 g, 1.313 mmol, 1.0 equiv), 2-iodopyrazine (0.352 g, 1.707 mmol, 1.3 equiv), 4M Cs2CO3 (1.15 mL, 4.60 mmol, 3.5 equiv) and PdCl2(dppf) (0.096 g, 0.131 mmol, 0.1 equiv) in DMF (6.5 mL) was combined and stirred at room temperature overnight. The reaction was partitioned between EtOAc and saturated aqueous NaHCO3, washed with water, brine, dried over MgSO4, and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc/hexanes) to provide 3-2 as a solid. ESI+ MS [M+H]+ C18H17N3O2: 263.01 found, 263.70 required. The reaction was partitioned between EtOAc and saturated aqueous NaHCO3 washed with water, brine dried over MgSO4 concentrated by rotary evaporation The residue was purified by column chromatography on silica gel (EtOAc/hexanes)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 39.8 g (110.0 mmol) of 3-bromo-8,8-dimethyl-8H-indolo[3,2,1-de]acridine (Br-1), 30 g (110.0 mmol) of [4-chloro-2-(ethoxycarbonyl)phenyl]boronic acid and 9.7 g (92 mmol) of sodium carbonate are suspended in 350 ml of toluene, 350 ml of dioxane and 500 ml of water. 913 mg (3.0 mmol) of tri-otolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to this suspension, and the reaction mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, filtered through silica gel, washed three times with 200 ml of water and subsequently evaporated to dryness. The residue is recrystallised from toluene. The yield is 44 g (94 mmol), corresponding to 86% of theory. the reaction mixture is heated under reflux for 16 h After cooling the organic phase is separated off filtered through silica gel washed three times with 200 ml of water subsequently evaporated to dryness The residue is recrystallised from toluene