Cesium carbonate → HCID 66600037, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(6-chloro-2-methylpyrimidin-4-yl)acetamide (228 mg, 1228 μmol), 3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (294 mg, 1228 μmol, Combi-Blocks, Inc., San Diego, Calif.), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) (100 mg, 123 μmol), cesium carbonate (197 μl, 2457 μmol), dioxane (4 mL) and water (0.5 mL) was stirred at 100° C. for 30 min. The mixture was cooled down to room temperature. The reaction mixture was diluted with saturated NH4Cl (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography eluting with EtOAc to give N-(6-(3-chloropyridin-4-yl)-2-methylpyrimidin-4-yl)acetamide (102 mg, 31.6% yield). 1H NMR (300 MHz, CDCl3) δ 8.80 (s, 1H); 8.56 (d, J=5.41 Hz, 1H); 8.34 (s, 1H); 7.94 (s, 1H); 7.44 (d, J=5.26 Hz, 1H); 2.69 (s, 3H); 2.25 (s, 3H). m/z (ESI, +ve ion) 263 (M+H)+.

Provenance & Evidence