2-(Tributylstannyl)pyridine → HCID 58026045, compound

Participants

Reaction Conditions

Reaction Steps

To a 350 mL sealable flask was added t-butyl 5-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (3.67 g, 11.77 mmol) and tri-n-butyl(2-pyridyl)tin (5.2 g, 14.12 mmol. The mixture was dissolved in dioxane (100 mL) and tetrakis(triphenylphosphine)palladium(0) (2.72 g, 2.354 mmol) was added. The mixture was flushed with N2 and the flask was sealed and heated to 110° C. After heating the mixture for 65 h, the mixture was cooled to rt and was filtered through a pad of CELITE® to remove the solids. The CELITE® was washed with MeOH and the organic solution was concentrated under reduced pressure. The residue was purified using BIOTAGE® flash chromatography and a 10-50% EtOAc in hexanes gradient. The expected product, tert-butyl 5-(pyridin-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (3.33 g, 10.72 mmol, 91% yield), was isolated as a thick yellow oil. LC/MS: m/z 311.02 (M+H)+, 2.257 min (method 1). 1H NMR (500 MHz, chloroform-d) δ ppm 8.70 (d, J=4.88 Hz, 1H) 7.77 (t, J=7.32 Hz, 1H) 7.40 (d, J=7.93 Hz, 1H) 7.23-7.32 (m, 3H) 7.19 (br. s., 1H) 4.64 (br. s., 2H) 3.55 (br. s., 2H) 2.86 (t, J=5.95 Hz, 2H) 1.48 (br. s., 9H).

Provenance & Evidence