p-Toluenesulfonic acid → HCID 66743838, compound

Participants

Reaction Steps

A mixture of 3-amino-5-bromothiophene-2-carboxamide (221 mg, 1.0 mmol), 4,4,4-trifluorobutan-2-one (1.26 g, 10 mmol), PTSA (19.0 mg, 0.1 mmol) and acetic acid (2 mL) was microwave-irradiated at 120° C. for 1 h. Then, the mixture was poured into saturated aqueous NaHCO3 (100 mL). Extraction with EtOAc (100 mL), washing with brine, drying over MgSO4, filtration and concentration under reduced pressure gave a yellow solid. This residue was mixed with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (582 mg, 3.0 mmol), sodium carbonate (530 mg, 5.0 mmol), 1,2-dimethoxyethane (5 mL) and water (2.5 mL). The mixture was purged with argon. Then, 1,1′-bis(diphenylphosphino)ferrocenepalladium (II) dichloride dichloromethane adduct (82 mg, 0.10 mmol) was added, and the mixture was purged with argon again. This mixture was refluxed for 6 h. Then, the mixture was poured into saturated aqueous NaHCO3 (200 mL) and EtOAc (200 mL), and the mixture was shaken well. The insoluble materials were filtered off. From the filtrate, the organic layer was collected, washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. This residue was purified by column chromatography (Purif, silica gel, 95:5 hexane/EtOAc to EtOAc) to afford a yellow solid (105 mg). This solid was triturated with EtOAc/hexane and collected by filtration to afford the title compound (89.3 mg, 28%) as a yellow solid:

Provenance & Evidence