Iodine → HCID 68183030, compound

Participants

Reaction Steps

5-chloro-2-[2-(morpholin-4-yl)-4-oxo-5,6-dihydro-4H-[1,3]thiazolo[5,4-c]azepin-8-yl]benzoic acid (0.0500 g, 0.123 mmol) was dissolved in acetonitrile (0.50 mL) and saturated aqueous sodium bicarbonate solution (2.5 mL), then added a solution of potassium iodide (0.102 g, 0.616 mmol) and iodine (0.0406 g, 0.160 mmol) in water (1.0 mL) dropwise and the solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with EA and 15% aqueous sodium thiosulfate solution and the mixture was stirred for 20 minutes. 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 (0.0540 g, 82%). LCMS: (AA) ES+ 532, 534. 1H NMR (400 MHz, d6-DMSO) δ: 8.44 (t, J=4.8 Hz, 1H), 8.07-7.90 (m, 1H), 7.92-7.72 (m, 2H), 5.12-4.91 (m, 1H), 3.93-3.81 (m, 1H), 3.77-3.65 (m, 1H), 3.61-3.48 (m, 4H), 3.23-3.08 (m, 4H).

Provenance & Evidence