Sodium Carbonate → HCID 68304375, compound

Participants

Reaction Conditions

Reaction Steps

3-Bromo-6-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine (200 mg, 0.752 mmol), methyl-5-methyl-4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-thiophene-2-carboxylate (297 mg, 1.05 mmol), Pd(PPh3)4 (43.4 mg, 0.038 mmol), and 2 M sodium carbonate (aq) (750 μL, 1.50 mmol) were placed in a sealed tube. 1,4-dioxane (3.75 mL) was added and the reaction purged with N2 for 5 min. The reaction was heated to 85° C. for 7 h. After consumption of starting material, the reaction was cooled to room temperature, diluted with water and extracted 3× with ethyl acetate. The organic layers were combined, washed with brine, dried with sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (0-70% EtOAc/Hex) to afford the title compound (120 mg, 0.352 mmol). LRMS (APCI) calc'd for (C14H10F3N3O2S) [M+H]+, 342.0; found 342.0.

Provenance & Evidence