Ethanol → HCID 58754823, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 50.0 mg (0.156 mmol) of 2-bromo-4-(morpholine-4-sulfonyl)-phenylamine (as prepared in the previous step) in toluene (4 mL) and EtOH (2 mL) was treated with 623 μL (1.25 mmol) of 2.0 M aqueous Na2CO3 and 20.6 mg (0.163 mmol) of cyclohex-1-enylboronic acid. The mixture was degassed via sonication, placed under Ar, treated with 12.6 mg (0.0109 mmol) of Pd(PPh3)4, and heated to 80° C. for 3.5 h. The mixture was cooled to RT, stirred for 16 h, diluted with EtOAc (10 mL) and washed with saturated aqueous NaHCO3 (1×10 mL) and brine (1×10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 25-g Varian MegaBond Elut SPE column with 25-50% EtOAc-hexane afforded 20.0 mg (40%) of the title compound as an off-white solid: Mass spectrum (ESI, m/z): Calcd. for C16H22N2O3S, 323.1 (M+H), found 323.1.

Provenance & Evidence