1,4-Dioxane → HCID 57708048, compound

Participants

Reaction Steps

A solution of (S)-2-(1-(2,8-dichloroquinolin-3-yl)ethyl)isoindoline-1,3-dione (0.2000 g, 0.5388 mmol), 5-(tributylstannyl)thiazole (0.4032 g, 1.078 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.06226 g, 0.05388 mmol) in 1,4-dioxane (4.490 mL, 0.5388 mmol) was stirred at 100° C. After 94 h, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on a 40 g of Redi-Sep™ column using 0 to 100% gradient of EtOAc in hexane over 14 min and then 100% isocratic of EtOAc for 7 min as eluent to give 2-((S)-1-(8-chloro-2-(thiazol-5-yl)-quinolin-3-yl)ethyl)isoindoline-1,3-dione as a light yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 9.10 (1H, s), 8.83 (1H, s), 8.30 (1H, d, J=0.8 Hz), 8.13 (1H, dd, J=8.2, 1.2 Hz), 7.99 (1H, dd, J=7.6, 1.4 Hz), 7.71-7.82 (4H, m), 7.60-7.69 (1H, m), 6.03 (1H, q, J=7.2 Hz), 1.88 (3H, d, J=7.0 Hz); LC-MS (ESI) m/z 420.1 [M+H]+.

Provenance & Evidence