p-Toluenesulfonic acid → HCID 86686190, compound

Participants

Reaction Steps

A solution of 2-[2-(6-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-phenylsulfanyl]-ethanol (400 mg, 1.38 mmol), 4-methylbenzenesulfonic acid (65 mg, 0.345 mmol) and 3,4-dihydro-2H-pyran (251 μL, 2.76 mmol) in DCM (5 mL) was stirred at RT under a nitrogen atmosphere for 36 h. The reaction mixture was diluted with DCM and extracted with sat. NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by FCC using MeOH in DCM (0 to 5%) to give the title compound as a pale yellow oil (381 mg, 74%). LCMS (Method 3): Rt 3.10 min, m/z 374 [MH+]. 1H NMR (400 MHz, CDCl3): 1.49 (6 H, m), 3.01-3.02 (2 H, m), 3.42-3.59 (2 H, m), 3.80-3.80 (2 H, m), 4.52 (1 H, m), 7.34-7.35 (2 H, m), 7.55-7.55 (2 H, m), 7.67-7.68 (2 H, m), 7.90 (1 H, dd, J 9.97 and 4.82).

Provenance & Evidence