Continuously updated synthesis method about 4-Iodo-1-trityl-1H-imidazole

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-1-trityl-1H-imidazole, and friends who are interested can also refer to it.

Electric Literature of 96797-15-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 96797-15-8 name is 4-Iodo-1-trityl-1H-imidazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-IODO-L-TRITYL-LH- imidazole (15.0 g, 34 mmoles) in THF (150 ml) at room temperature was added ethylmagnesium bromide (41 ml, 40.7 mmoles) under dry conditions. After stirring for 90 minutes, zinc chloride (5.6 g, 40.7 mmoles) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis (RIPHENYLPHOSPHINE) palladium (4.0 g, 3.43 mmoles) and 5-bromo-2-methylpyridine (7.0 g, 40.7 mmoles) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70C oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane and washed with an EDTA buffer (at APPROIMATE pH 9) (2x 300 ML), NACI (sat. ) (300 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was dissolved in ethanol (250 ml) and concentrated HCl (13.6 ml) was added to the solution at room temperature. The reaction mixture was heated in a 50C oil bath for 2 hours. Upon cooling, the reaction was filtered and washed with ethyl ether (25 ml) to yield 5- (1H- imidazol-4-yl) -2-methyl-pyridine (5.815g, 63%). MH+ (160).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-1-trityl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Patent; CHIRON CORPORATION; WO2004/96823; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem