Sodium Carbonate → HCID 117667637, compound

Participants

Reaction Conditions

Reaction Steps

A vial containing 1-(5-bromo-pyridin-3-yl)-ethanone (1.59 g, 8.0 mmol), bis(pinacolato)diboron (2.53 g, 9.9 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) DCM complex (486 mg, 0.66 mmol) and potassium acetate (1.96 g, 19.9 mmol) in 1,4-dioxane (100 mL) is flushed with Ar, sealed tightly and heated to 70° C. for 16 h. The reaction mixture is cooled to room temperature and 6-bromo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (2.08 g, 6.6 mmol), aqueous sodium carbonate solution (2M, 9.9 mL, 19.9 mmol) and additional 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (486 mg, 0.66 mmol) are added. The mixture is flushed with Ar, sealed tightly and heated to 100° C. for 2 h. The reaction mixture is cooled to room temperature and partitioned between water and EtOAc. The layers are separated and the aqueous is further extracted with EtOAc. The combined organic layers are washed with brine and filtered through diatomaceous earth, rinsing well with EtOAc. The filtrate is dried (Na2SO4) and concentrated. The crude product is purified by silica gel column (25-100% EtOAc in heptane) to afford 6-(5-acetyl-pyridin-3-yl)-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (1.85 g).

Provenance & Evidence