Sodium Carbonate → Methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (200.0 mg, 0.600 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (188.8 mg, 0.6107 mmol) in DME (5.15 mL) was treated with Na2CO3 (2.00 M in water, 0.83 mL, 1.66 mmol). The mixture was degassed and Pd(Ph3P)4 (13 mg, 0.011 mmol) was added. The reaction mixture was heated under argon at 80° C. overnight. The mixture was then cooled to room temperature and diluted with water. The aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (SiO2, 10-50% EtOAc in hexanes) to give methyl 2-{4-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (228 mg, 89%). LC-MS: (FA) ES+ 263.

Provenance & Evidence