Ethyl Acetate → HCID 178480541, compound

Participants

Reaction Steps

N-(((2,4-Difluoro-3-methoxyphenyl)amino)((3-(3-fluoro-4-methoxyphenyl)-1H-pyrazol-5-yl)amino)methylene)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (110 mg, 0.194 mmol) was suspended in dichloromethane (4 mL), and a solution of boron tribromide in DCM (1 mL of 1 M, 5 equivalents) was added carefully. The mixture was stirred at room temperature overnight. Then, the reaction was quenched by the addition of ice, and the resulting slurry was then treated with aqueous sodium bicarbonate (pH approximately neutral). The mixture was stirred for 30 minutes, and then partitioned between water and EtOAc. Next, the organic phase was dried over sodium sulfate, and concentrated onto silica gel. The crude product was purified by chromatography (gradient: 8:2 hexanes:EtOAc to 2:8 hexanes:EtOAc to provide the title compound as a white solid (29 mg, 28% yield). 1H NMR (DMSO-d6) δ 13.16 (s, 1H), 12.69 (s, 1H), 10.72 (s, 1H), 10.32 (s, 1H), 10.23 (s, 1H), 8.09 (s, 1H), 7.56 (m, 2H), 7.40 (d, 1H), 7.04 (m, 2H), 6.62 (s, 1H), 3.89 (s, 3H). MS: calc.=539.39; obs. M+H=540.03. HPLC (Method E): retention time was 4.828 minutes.

Provenance & Evidence