Dimethylformamide → HCID 16128760, compound

Participants

Reaction Steps

1-(3-Nitro-phenyl)-1H-imidazole-4-carboxylic acid 21 (0.1 g, 0.4 mmol) was suspended in CH2Cl2 (5 mL) and a drop of DMF (cat.) was added. Then oxalyl chloride (111 μL, 1.29 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The organic layer was removed by decantation and the remaining solid was washed twice with CH2Cl2. The solid was suspended in CH2Cl2 and 3-hydroxypyridine was added dropwise. The clear solution was stirred at room temperature for 2 h after which 1N NaOH (aq) was added and the layers were separated. Concentration of the organic layer followed by column chromatography on silica gel with 5% MeOH in CH2Cl2 afforded 14 mg (10%) of 22 as a white solid. HRMS (ESI+): m/z=310.268 [M+H]

Provenance & Evidence