Sodium Carbonate → HCID 67260872, compound

Participants

Reaction Steps

To a mixture of 1-methyl-3-(3-methyl-2-thienyl)-5-propyl-1H-pyrazole and 1-methyl-5-(3-methyl-2-thienyl)-3-propyl-1H-pyrazole (85:15, 3.7 mmol) in 10 mL dry N,N-dimethylformamide under argon atmosphere was added N-iodosuccinimide (4.6 mmol) in small portions. The reaction mixture was stirred at room temperature overnight. 5% aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate solution were added and the mixture was stirred at room temperature for 1 h, then extracted with MTBE. The combined organic extracts were successively washed with water and brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (toluene:ethyl acetate 100:0 to 0:100) to afford 928 mg of a mixture of 4-iodo-1-methyl-3-(3-methyl-2-thienyl)-5-propyl-1H-pyrazole and 4-iodo-1-methyl-5-(3-methyl-2-thienyl)-3-propyl-1H-pyrazole (85:15; 61% yield) that was used in the next step without further purification.

Provenance & Evidence