The Synthetic Routes of N-Methyl-N-(phenylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine

N-Methyl-N-(phenylmethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine (M1) is an important organoborane compound that has been widely used in various fields, such as medicine, agrochemicals, and materials science.
Its unique structure and properties make it a promising material for the development of new drugs, pesticides, and materials.

The synthesis of M1 can be achieved through several routes, including the classical synthesis route and the newer synthesis routes.
In this article, we will discuss the synthetic routes of M1 in the chemical industry.

Classical Synthesis Route

The classical synthesis route of M1 involves several steps, including the synthesis of boronate ester, reduction of the boronate ester to boronic acid, and finally the nucleophilic substitution of the boronic acid with N-methyl-N-(phenylmethyl)amine.

The synthesis of boronate ester involves the reaction of boric acid with a phenol in the presence of an alkali hydroxide.
The reaction produces a phenoxyborate ester, which can be purified and then reduced to boronic acid using hydrogen in the presence of a metal catalyst, such as palladium on barium oxide.

The nucleophilic substitution of boronic acid with N-methyl-N-(phenylmethyl)amine can be carried out using several nucleophiles, such as ammonia or an alcohol.
The reaction involves the formation of a boronate ester intermediate, which can then be hydrolyzed to produce M1.

Newer Synthesis Routes

In recent years, several newer synthesis routes for M1 have been developed, which offer more efficient and economical methods for the synthesis of this compound.
These routes include the use of microwaves, microwave-assisted hydroboration, and Suzuki-Miyaura coupling.

Microwave-assisted Synthesis Route

The microwave-assisted synthesis route of M1 involves the use of microwave irradiation during the synthesis process.
In this route, the boronate ester is synthesized using boric acid and a phenol in the presence of a microwave catalyst, such as sodium hydroxide.
The resulting boronate ester can then be reduced to boronic acid using hydrogen in the presence of a metal catalyst, such as palladium on barium oxide.
The boronic acid can then be nucleophilically substituted with N-methyl-N-(phenylmethyl)amine in the presence of a base, such as sodium hydroxide, to produce M1.

Microwave-assisted hydroboration

The microwave-assisted hydroboration synthesis route of M1 involves the use of borane reagents and microwave irradiation during the synthesis process.
In this route, the boronate ester is synthesized using boric acid and a phenol in the presence of a borane reagent, such as diborane or borane-dimethyl sulfide.
The resulting boronate ester can then be reduced to boronic acid using hydrogen in the presence of a metal catalyst, such as palladium on barium oxide.
The boronic acid can then be nucleophilically substituted with N-methyl-N-(phenylmethyl)amine in the presence of a base, such as sodium hydroxide, to produce M1.

Suzuki-Miyaura Coupling

The Suzuki-Miyaura coupling synthesis route of M1 involves the use of a palladium catalyst and a boronate ester as the starting material.
In this route, the boronate ester is