Potassium Carbonate → 5-[2-(4-Methoxybenzylamino)pyridin-6-yl]pentanoic acid ethyl ester

Participants

Reaction Steps

Ethyl 4-pentenoate (8.95 g, 69.8 mmol) was treated with 9-BBN (167 mL, 83.7 mmol; 0.5M in THF) at 0° C. then warmed to room temperature and stirred for 16 hours. To this solution was added Pd(OAc)2 (1.57 g, 6.98 mmol), pyridine 16-2 (18.4 g, 62.8 mmol), K2CO3 (14.4 g, 105 mmol), 1,1′-bis(diphenylphosphino)-ferrocene (3.87 g, 6.98 mmol) and DMF (200 mL). The mixture was degassed with argon for 10 minutes then heated to 80° C. for 24 hours. The reaction mixture was cooled and stirred with ethanolamine (20 mL) for 2 hours. The mixture was partitioned between water and EtOAc, extracted with EtOAc (3×), washed with water (3×), then brine, dried (MgSO4) and concentrated. Purification by silica gel chromatography (hexane:EtOAc 3:2) afforded the title compound 16-3 as an oil.

Provenance & Evidence