The Production Process of N-Cyclohexyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine

The production process of N-cyclohexyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine involves several steps, including the synthesis of the starting materials, the formation of the intermediate compounds, and the purification and isolation of the final product.

1. Synthesis of starting materials

The production of N-cyclohexyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine requires the synthesis of several starting materials, including the precursor to the dioxaborolane ligand, 4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the precursor to the pyridinamine ring, 2-aminopyridine.

4,4,5,5-tetramethyl-1,3,2-dioxaborolane can be synthesized by a variety of methods, including hydroboration of 1,3-dioxolane with borane, followed by reduction of the resulting boronic acid with lithium aluminum hydride (LiAlH4).
2-aminopyridine can be synthesized by a similar method, using ammonia and borane in the presence of a catalyst such as palladium on barium oxide.

1. Formation of intermediate compounds

Once the starting materials have been synthesized, the next step in the production process is the formation of the intermediate compounds.
In the case of N-cyclohexyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine, the intermediate compounds include the dioxaborolane ligand and the aminopyridine ring.

The dioxaborolane ligand can be introduced into the molecule by a process known as ligand exchange, in which the amino group of the aminopyridine ring is replaced by the dioxaborolane ligand.
This can be accomplished by treating the aminopyridine with borane in the presence of a catalyst, such as tetrakis(p-toluenesulfonamido) catalyst (TOSA).
The resulting intermediate compound is then treated with a Grignard reagent, such as cyclohexyl bromide, to introduce the methyl group onto the nitrogen atom.

1. Purification and isolation of the final product

After the intermediate compounds have been formed, the next step is to purify and isolate the final product, N-cyclohexyl-N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine.
This can be accomplished by a variety of methods, including recrystallization, chromatography, and distillation.

Recrystallization involves dissolving the crude product in a solvent, such as ethanol or water, and allowing the crystals to form through slow evaporation.
The resulting crystals are then collected and dried, resulting in a pure sample of the final product.

Chromatography involves passing the crude product through a column packed with a solid support, such as silica gel or activated carbon, and eluting the compound with a solvent or a mixture of solvents.
The different compounds in the mixture will elute at different rates, allowing for the separation and collection of the pure final product.

Distillation involves heating the crude product to a high temperature, causing the pure