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6-fluoroH-iMidazo[1,2-a]pyridin-3-carboxylic acid is an important intermediate in the synthesis of several pharmaceuticals, agrochemicals, and other chemical products.
The demand for this compound has been increasing steadily in recent years, making it an interesting subject for chemical synthesis and manufacturing.
There are several synthetic routes to 6-fluoroH-iMidazo[1,2-a]pyridin-3-carboxylic acid, and the selection of the appropriate route depends on various factors such as the availability of starting materials, the scale of production, and the desired yield and purity of the product.
In this article, we will discuss some of the most commonly used synthetic routes to 6-fluoroH-iMidazo[1,2-a]pyridin-3-carboxylic acid.
Route 1: via N-fluoromethylation of 1H-imidazo[1,2-d]pyrimidine-2,5-diamine
This route involves the synthesis of N-fluoromethylated 1H-imidazo[1,2-d]pyrimidine-2,5-diamine, which is then hydrolyzed to yield 6-fluoroH-iMidazo[1,2-a]pyridin-3-carboxylic acid.
The synthesis of N-fluoromethylated 1H-imidazo[1,2-d]pyrimidine-2,5-diamine can be achieved by two methods: via N-fluoromethylation of 1H-imidazo[1,2-d]pyrimidine-2,5-diamine with N-fluorobenzensulfonic acid or N-fluoromesityl oxide, or via N-fluoromethylation of 1,2-diamino-3,4-dihydro-1H-imidazo[1,2-d]pyrimidin-5-one with N-fluoromethanesulfonic acid.
Route 2: via N-methylation of 1H-imidazo[1,2-c]pyridin-3-amine
This route involves the synthesis of N-methylated 1H-imidazo[1,2-c]pyridin-3-amine, which is then deamidated to yield 6-fluoroH-iMidazo[1,2-a]pyridin-3-carboxylic acid.
The synthesis of N-methylated 1H-imidazo[1,2-c]pyridin-3-amine can be achieved by several methods, such as N-methylation with methyl iodide or N-methylation with methylamine followed by reduction with lithium aluminum hydride.
Route 3: via N-chlorination of 1,3-dihydro-1H-imidazo[1,2-d]pyrimidine-2-one
This route involves the synthesis of N-chlorinated 1,3-dihydro-1H-imidazo[1,2-d]pyrimidine-2-one, which is then hydrolyzed to yield 6-fluoroH-iMidazo[1,2-a]pyridin-3-carboxylic acid.
The synthesis of N-chlorinated 1,3-dihydro-1H-imidazo[1,2-d]pyrimidine-2-one can be achieved by several methods, such as N-chlorination with chloroformic acid or N