Toluene → HCID 23125017, compound

Participants

Reaction Steps

4-(t-Butoxycarbonyl)-2-nitrobenzoic acid (1.0 g) is dissolved in tetrahydrofuran (50 ml), and thereto is added 28% sodium methoxide in methanol (0.72 g). After pouring toluene, the mixture is concentrated under reduced pressure. The resulting residue is suspended in chloroform (50 ml), and thereto are added oxalyl chloride (489 μl) and N,N-dimethylformamide (2 drops) followed by stirring at room temperature for 3 hours. The reaction solution is concentrated under reduced pressure, and chloroform (20 ml) is poured to the residue to give a suspension. 5-Chloro-2-aminopyridine (480 mg) and pyridine (453 μl) are dissolved in chloroform (30 ml), and the solution is ice-cooled. To the solution is added dropwise the suspension prepared above. The reaction solution is stirred at room temperature for 8 hours and concentrated under reduced pressure. The residue is diluted with ethyl acetate, washed successively with 10% aqueous potassium hydrogen sulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to give t-butyl 4-{[(5-chloropyridin-2-yl)amino]carbonyl}-3-nitrobenzoate (803 mg). APCI-MS M/Z: 378[M+H]+

Provenance & Evidence