Water → HCID 57937593, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-nitroaniline (1.0 g, 4.6 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.1 g, 5.1 mmol) were dissolved in 13 ml of DMA, placed under nitrogen, and heated to 80° C. A 2N aqueous solution of Na2CO3 was added, followed by PdCl2(dppf) dichloromethane adduct (0.076 g, 0.90 mmol). Reaction was stirred at 80° C. for 1 h and then cooled to rt, poured into 150 ml of water and extracted with EtOAc (3×), Combined organics were dried over anhydrous MgSO4, filtered, concentrated onto silica gel, and purified by flash chromatography using 0-50% EtOAc/hexanes. 4-(1-Methyl-1H-pyrazol-4-yl)-2-nitroaniline was isolated as a bright orange solid (1.0 g, 99%). MS (ESI): 219 [M+H]+.

Provenance & Evidence