Potassium Carbonate → HCID 59633327, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL round bottom flask attached with condenser was added 1-(2-Bromo-phenyl)-5-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-3-trifluoromethyl-1H-pyrazole (prepared following the described in Example 1c) (110 mg, 210 μmol), 3-pyridylboronic acid (31 mg, 525 μmol), PdCl2dppf (25 mg, 10 mol %), K2CO3 (58 mg, 410 μmol), 1,4-dioxane (8 mL) and H2O (1.5 mL). The reaction solution was allowed to stir at 75° C. for 20 hrs. The reaction solution was diluted with EtOAc (150 mL) and transferred to a separator), funnel and washed with aq NH4Cl (100 mL) and aq NaCl (100 mL). The organic phase was dried over Na2SO4, filtered, concentrated on the Rotavapor and chromatographed through a 25 g SiO2 column using a mobile phase gradient of 100% Hx to 90% EtOAc to afford 45 mg (41% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.41 (m, 1H), 7.99 (m, 2H), 7.51-7.90 (m, 8H), 7.24 (s, 1H), 7.17-7.23 (m, 2H), 6.87 (d, 1H), 3.28 (s, 3H); 19F NMR (400 MHz, DMSO-d6) δ −61.2 ppm. MS (ES) 526.5 [M+H]+.

Provenance & Evidence