Dichloromethane → HCID 58577826, compound

Participants

Reaction Steps

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (40.8 mg, 0.05 mmol) and an aqueous solution of potassium carbonate (0.72 g, 4 mmol in 1.0 mL of water) were successively added to a solution of 7-bromo-2-methylquinoline-4-carboxylic acid B-14 (0.26 g, 1.00 mmol) and methyl 2,2-dimethyl-3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)propanoate A-7 (0.43 g, 1.50 mmol) in isopropanol (5.0 mL) and 1,4-dioxane (20 mL). The reaction was degassed several times under reduced pressure, placed under a nitrogen atmosphere and stirred at room temperature for 24 h. After quenching with a 1 N aqueous hydrogen chloride solution (2.0 mL), the mixture was filtered through a celite pad, washed with ethyl acetate (100 mL) and concentrated to dryness under reduced pressure. The residue was purified by flash column chromatography on silica gel (20:1 CH2Cl2:MeOH) to give 7-(6-(3-methoxy-2,2-dimethyl-3-oxopropoxy)pyridin-3-yl)-2-methylquinoline-4-carboxylic acid B-15 as a brown solid (0.32 g, Yield=82%). MS (ESI), [M+1]+ 395.

Provenance & Evidence