Cesium fluoride → HCID 68183056, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(morpholin-4-yl)-8-(trimethylstannyl)-5,6-dihydro-4H-[1,3]thiazolo[5,4-c]azepin-4-one (0.160 g, 0.386 mmol) and methyl-5-bromo-2-chlorobenzoate (0.116 g, 0.464 mmol) in DMF (3.74 mL) was purged with argon, and then cesium fluoride (0.205 g, 1.35 mmol), copper(I) iodide (0.0184 g, 0.0966 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0446 g, 0.0386 mmol) were added. The mixture was stirred at 80° C. for 2 hours. The solution was cooled to room temperature and some of the solvent was removed in vacuo. The residue was diluted with EA and water. The layers were separated and the aqueous layer was extracted twice more with EA. The combined organic layer was then washed with water and brine then dried over anhydrous sodium sulfate and concentrated. The residue was purified using column chromatography on silica gel (12 gr Analogix column, gradient DCM to 60% EA in DCM over 15 minutes) to give the product (0.129 g, 80%). LCMS: (AA) ES+ 420, 422. 1H NMR (400 MHz, d6-DMSO) δ: 8.05 (t, J=5.0 Hz, 1H), 7.80 (d, J=2.1 Hz, 1H), 7.61-7.44 (m, 2H), 6.48 (t, J=7.1 Hz, 1H), 3.84 (s, 3H), 3.70-3.62 (m, 4H), 3.61-3.53 (m, 2H), 3.42-3.34 (m, 4H).

Provenance & Evidence