2-Methyl-6-(tributylstannyl)pyridine → 2-((S)-1-(8-Chloro-2-(6-methylpyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of (S)-2-(1-(2,8-dichloroquinolin-3-yl)ethyl)isoindoline-1,3-dione (254.3 mg, 0.685 mmol) and tetrakis(triphenylphosphine)palladium (79.16 mg, 68.50 μmol), 2-methyl-6-(tributylstannyl)pyridine (523.6 mg, 1.37 mmol) in dioxane (degassed) was heated at 100° C. for 28 h, complete by LC-MS solvent removed and chromatographed: 89:9:1 (DCM/MeOH,NH4OH)gradient. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.78 (1H, s), 8.15 (1H, dd, J=8.3, 1.3 Hz), 7.98 (1H, dd, J=7.5, 1.3 Hz), 7.73-7.78 (2H, m), 7.58-7.69 (4H, m), 7.36 (1H, d, J=7.6 Hz), 7.16 (1H, d, J=7.6 Hz), 6.11-6.19 (1H, m), 2.33 (3H, s), 1.82 (3H, d, J=7.0 Hz)

Provenance & Evidence