Potassium Carbonate → HCID 118006176, compound

Participants

Reaction Steps

A suspension of (2,4-dichloro-3-(4-(methylthio)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (1.10 g, 2.00 mmol, Example 95), 3-chloroperbenzoic acid (˜77%, 1.62 g, 7.23 mmol) and DCM (100 mL) was stirred at room temperature for 2.5 hours, during which it became a clear solution. LCMS showed mainly methylsulfonate product and methylsulfonyl pyridine-oxide by-product. To the mixture was added tribromophosphine (1.0 M in DCM, 3.2 mL, 3.2 mmol) dropwise (a white suspension formed at the end of the addition). DMF (10 mL) was then added and the suspension dissolved. After stirring for ˜30 minutes, additional tribromophosphine (1.0 M in DCM, 3.2 mL, 3.2 mmol) was added. After stirring for 1 hour, 1 M K2CO3 (aqueous) was added, the organic layer was separated. The aqueous layer was further extracted with DCM. The combined organic phases were washed with 1 M K2CO3 (aqueous), and the aqueous layer was back extracted with DCM. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 30-100% EtOAc in heptanes, 10% MeOH in DCM) to provide the title compound. 1H NMR (400 MHz, CHLOROFORM-d) δ 8.25 (d, J=2.02 Hz, 1H), 8.02 (d, J=9.09 Hz, 1H), 7.93 (br. s., 1H), 7.86 (d, J=8.59 Hz, 2H), 7.58 (dd, J=2.27, 8.84 Hz, 1H), 7.44 (d, J=8.59 Hz, 2H), 6.91-6.98 (m, 2H), 6.87 (s, 1H), 4.61 (s, 2H), 3.94 (s, 3H), 3.03 (s, 3H), 2.54 (s, 3H), 2.36 (s, 3H); MS m/e 582.2 [M+H]+.

Provenance & Evidence