Tetrahydrofuran → HCID 12043694, compound

Participants

Reaction Conditions

Reaction Steps

To the solution of 3-(trifluoromethyl)-1-(3-cyanophenyl)-1H-pyrazolecarboxylic acid (0.2 g, 0.6 mmol) in dry acetonitrile (10 mL) was added thionyl chloride (0.37 g, 1.8 mmol). The reaction mixture was warmed up to 50° C. for 1 h. The solvent and excess thionyl chloride were removed under reduced pressure and dried on a vacuum pump over 18 h. This residue was dissolved in THF and treated with a mixture of 2-(2,3-dihydro-1H-indol-5-yl)-N-(1,1-dimethylethyl)benzenesulfonamide from Example 1 (0.3 g, 0.8 mmol) in THF (5 mL) and NaH (72 mg, 1.6 mmol). The reaction mixture was allowed to stir at ambient temperature for 0.5 h, then quenched with water and extracted with EtOAc (3×). Ethyl acetate extracts were dried over sodium sulfate and concentrated. The crude residue was purified by flash chromatography (hexane/EtOAc, 1:3) to afford the title product (0.38 g, 92%). LRMS (ES+): 593.2 (M+H)+.

Provenance & Evidence