Potassium Carbonate → Ethyl 5-(4-chloro-3-methyl-[1,8]-naphthyridin-2-yl)pentanoate

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To a solution of ethyl 4-pentenoate (2.5 g, 20 mmol) in 60 mL THF was added 9-BBN (0.5 M in THF, 47 mL, 23 mmol) gradually at room temperature. After stirring for 10 hours, it was treated with Pd(OAc)2 (0.4 g, 2.0 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (DPPF) (1.1 g, 2.0 mmol), K2CO3 (powder, 8.1 g, 58 mmol), 2,4-dichloro-3-methyl-naphthyridine (L) (3.6 g, 20 mmol) and 50 mL DMF. The reaction mixture was purged with argon for 5 minutes and then refluxed at 75° C. for 24 hours. It was cooled to room temperature and treated with 10 mL ethanolamine and stirred for 30 minutes. The mixture was diluted with 400 mL H2O and extracted with EtOAc(×3). The combined organic layers were washed with brine and dried. After solvent removal, the residue was purified by silica gel chromatography using EtOAc/hexanes (1:1) to give the desired product 3-3 as a liquid.

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