“…The condensation/cyclization of α-diketones, α-hydroxyketones, α-halogenoketones, α-aminoketones, α-haloesters, or α-oximinoketones with excess formamide at high temperatures is known as the Bredereck reaction (Scheme ). − This route has been successful in the preparation of 4,5-disubstituted imidazoles with yields varying between 40 and 90%. − However, the reproducibility of this method has been debated, and some investigators found yields as low as 20−30% for various 4,5-disubstituted imidazoles. , 1 …”
Automated process development technology was applied to the synthesis of 4(5)-(3-pyridyl)imidazole. This method utilizes automated liquid handling equipment coupled with statistically designed protocols for rapid process optimization. Two experimental sets were carried out based on a three-level factorial and central composite designs to optimise the product yield. The central composite design was repeated on one-fifth the scale to test the capabilities of the automated equipment. The reaction variables investigated were temperature and stoichiometry of formamide. The optimum in situ yield of 4(5)-(3-pyridyl)imidazole was found to be at 160 °C and 9 equiv of formamide. The results from the automated technology can be applied to larger-scale synthesis of the desired compound.
“…The condensation/cyclization of α-diketones, α-hydroxyketones, α-halogenoketones, α-aminoketones, α-haloesters, or α-oximinoketones with excess formamide at high temperatures is known as the Bredereck reaction (Scheme ). − This route has been successful in the preparation of 4,5-disubstituted imidazoles with yields varying between 40 and 90%. − However, the reproducibility of this method has been debated, and some investigators found yields as low as 20−30% for various 4,5-disubstituted imidazoles. , 1 …”
Automated process development technology was applied to the synthesis of 4(5)-(3-pyridyl)imidazole. This method utilizes automated liquid handling equipment coupled with statistically designed protocols for rapid process optimization. Two experimental sets were carried out based on a three-level factorial and central composite designs to optimise the product yield. The central composite design was repeated on one-fifth the scale to test the capabilities of the automated equipment. The reaction variables investigated were temperature and stoichiometry of formamide. The optimum in situ yield of 4(5)-(3-pyridyl)imidazole was found to be at 160 °C and 9 equiv of formamide. The results from the automated technology can be applied to larger-scale synthesis of the desired compound.
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