Lawesson's reagent → HCID 178480327, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 24 (300 mg, 0.571 mmol) in toluene (6 mL) at ambient temperature was added Lawesson's Reagent (231 mg, 0.571 mmol). This mixture was warmed to 95° C. and allowed to stir for 4 hours. The mixture was then cooled to ambient temperature, concentrated under reduced pressure. The residue was dissolved in EtOAc (20 mL) and washed with NaHCO3 solution. The organics were combined, dried, concentrated, and the residue was purified by Analogix® Intelliflash280™ (SiO2, 0-10% (7 M ammonia in methanol) in CH2Cl2 over 25 min) to obtain the title compound in 87% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.37 (s, 9 H) 1.47-1.63 (m, 4 H) 1.73-1.89 (m, 4 H) 2.10 (q, J=8.59 Hz, 1 H) 2.19 (s, 3 H) 2.38-2.47 (m, 1 H) 2.81-2.90 (m, 1 H) 3.59-3.67 (m, 1 H) 3.71-3.81 (m, 1 H) 3.96 (ddd, J=14.67, 9.41, 5.76 Hz, 2 H) 4.27-4.34 (m, 3 H) 7.23 (d, J=8.82 Hz, 1 H) 7.55-7.59 (m, 2 H) 7.63 (dd, J=8.82, 2.03 Hz, 1 H); MS (DCI/NH3) m/z 542 (M+H)+.

Provenance & Evidence