Sodium Iodide → HCID 21094019, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-mercaptophenyl)-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide (see EXAMPLE 146, 349 mg, 1.0 mmol), K2CO3 (152 mg, 1.1 mmol), NaI (150 mg, 1.0 mmol), and 3-(tosyloxy)oxetane (274 mg, 1.2 mmol) in anhydrous DMAc (20 mL) was heated for 2 h at 130° C. The solvent was evaporated off under reduced pressure, then the residue was partitioned between CH2Cl2 (75 mL) and 2% aqueous citric acid (20 mL). The organic layer was washed with H2O (20 mL), saturated aqueous Na2CO3 (20 mL), and brine (20 mL), before being dried (MgSO4). Filtration and solvent evaporation afforded 2-[4-(oxetan-3-ylsulfanyl)phenyl]-3-(tetrahydropyran-4-yl)-N-thiazol-2-ylpropionamide: m/z (ES+)=405.2 [M+H]+. This thioether was oxidised employing the protocol outlined in EXAMPLE 148 to give the title compound: RTA=3.04 min; m/z (ES+)=437.2 [M+H]+.

Provenance & Evidence