Sodium Carbonate → HCID 58387731, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 5-formyl-4-methylthiophen-2-ylboronic acid (2.21 g, 13.0 mmol, commercially available), 2-bromo-5-chloropyridine (2.00 g, 10.4 mmol, commercially available) and 2 N Na2CO3 (10.4 mL, 20.8 mmol) in DMF (70.2 mL) was added PdCl2dppf (0.380 g, 0.520 mmol); the flask degassed and heated to 80° C. for 2.0 h. Upon cooling, the reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3×75 ml). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated and purified by flash chromatography (silica gel, CH2Cl2:EtOAc, 100:0 to 0:100) to afford 2.01 g of the title compound as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 9.96 (1H, s), 8.57 (1H, s), 7.98 (2H, s), 7.75 (1H, s), 2.49 (3H, s).HPLC retention time: 3.158 min; LCMS (ES): m/z 238 [M+H]+.

Provenance & Evidence