Dimethyl Sulfoxide → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-fluoropyridine-3-carbonyl chloride (180 mg, 0.5 mmol, Step B) and NaHCO3 (300 mg) in CH2Cl2 (5 ml), a solution of 4-{2,2,2-trifluoro-1-[2-(2-methoxy)ethoxy]-1-(trifluoromethyl)ethyl}phenylamine (95 mg) was added dropwise, and the suspension was stirred at RT for 1.5 h. Solid inorganic salts were removed via filtration. The filtrate was concentrated to afford (2-fluoro(3-pyridyl))-N-(4-{2,2,2-trifluoro-1-[2-(2-methoxyethoxy)ethoxy]-1-(trifluoromethyl)ethyl}phenyl)-carboxamide as a brown solid. (2-Fluoro(3-pyridyl))-N-(4-{2,2,2-trifluoro-1-[2-(2-methoxyethoxy)ethoxy]-1-(trifluoromethyl)ethyl}-phenyl)carboxamide (240 mg, 0.5 mmol) and 6-amino-indazole (133 mg, 1 mmol) were dissolved in DMSO (2 mL). The solution was heated to 120° C. for 8 h, then partitioned between CH2Cl2 and aqueous NaHCO3 (sat.). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified via preparative HPLC to give a yellow powder as a TFA salt of the title compound. MS: 598 (M+1). Calc'd. for C27H25F6N5O4−597.5.

Provenance & Evidence