Sulfoxonium, trimethyl-, iodide (1:1) → HCID 89783633, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium tert-butoxide (18.42 mg, 0.164 mmol) and trimethylsulfoxonium iodide (36.1 mg, 0.164 mmol) in anhydrous DMSO (0.5 mL) was stirred under argon at 25° C. for 10 min, providing a colorless solution. A solution of 2-(2-(1-phenylvinyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 113; 30 mg, 0.082 mmol) in DMSO (1.0 mL) was added (dropwise, over 2 min), and the resulting solution was stirred at 25° C. for 30 min. The reaction solution was diluted with LON aq. HCl (0.1 mL), then partitioned between DCM (50 mL) and water (20 mL). The aq. layer was extracted with additional DCM (20 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-10% MeOH/DCM) furnished 2-(2-(1-phenylcyclopropyl)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (18.8 mg, 0.050 mmol, 60% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 12.49 (1H, br. s.), 8.08 (1H, dd, J=7.4, 1.0 Hz), 8.00 (1H, d, J=8.6 Hz), 7.57 (1H, d, J=7.2 Hz), 7.44-7.50 (3H, m), 7.42 (2H, t, J=7.3 Hz), 7.33-7.38 (1H, m), 7.19 (1H, d, J=2.0 Hz), 7.07 (1H, d, J=8.8 Hz), 5.40 (1H, br. s.), 3.63 (2H, td, J=6.8, 2.2 Hz), 2.85 (2H, t, J=6.9 Hz), 1.68-1.72 (2H, m), 1.55-1.60 (2H, m). m/z (ESI, +ve) 380.1 (M+H)+.

Provenance & Evidence