Main applications of pyridine 4-toluenesulfonate_Kain Industrial Additives

Background and overview^[1]

Pyridine 4-methylbenzenesulfonate can be used as a pharmaceutical synthesis intermediate.

Apply^[1-3]

Pyridine 4-methylbenzenesulfonate can be used as a pharmaceutical synthesis intermediate. Examples of its application are as follows:

1) Prepare 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde. This method first prepares 3-bromo-4-[(3-fluorobenzyl)oxy ] benzaldehyde and pyridinium 4-methylbenzenesulfonate, and then react 3-bromo-4-[(3-fluorobenzyl)oxy]benzaldehyde with pyridinium-4-methylbenzenesulfonate to form 2- (3-bromo-4-((3-fluorobenzyl)oxy)phenyl)-1,3-dioxolane, followed by 2-(3-bromo-4-((3-fluorobenzyl) Oxy)phenyl)-1,3-dioxolane is hydroxylated to obtain 2-((3-fluorobenzyl)oxy)-5-formylphenylboronic acid, and finally 2-((3-fluorobenzyl) )oxy)-5-formylphenylboronic acid is coupled with m-fluorobenzyl bromide to obtain the target product. The invention provides a method for directly preparing 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde. The 3-(3-fluorobenzyl)-4-( The yield of 3-fluorobenzyloxy)benzaldehyde is as high as 64.85%, and the purity measured by high performance liquid chromatography reaches 98.92%.

2) Used to prepare the new compound 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane and its preparation method. This method first prepares 3 -Bromo-4-(3-fluorobenzyloxy)benzaldehyde with pyridinium 4-methylbenzenesulfonate, then 3-bromo-4-(3-fluorobenzyloxy)benzaldehyde with 4-methylbenzene Pyridinium sulfonate reacts to form 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane. The new compound 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane provided by the invention can be used to directly prepare 3-(3-fluorobenzyl)- 4-(3-fluorobenzyloxy)benzaldehyde, and the yield of the prepared 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde is as high as 64.85%, measured by high performance liquid chromatography The purity reaches 98.92%.

3) Used to prepare a new compound 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid. This method first prepares 3-bromo-4-[(3-fluorobenzyl)oxy base] benzaldehyde (formula 3) and pyridinium 4-methylbenzenesulfonate (formula 6), and then compound 3 reacts with compound 6 to generate 2-(3-bromo-4-(3-fluorobenzyloxy)phenyl )-1,3-dioxolane (Formula 7), compound 7 undergoes coupling reaction to obtain 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid (Formula 8). The new compound 2-(3-fluorobenzyloxy)-5-formylphenylboronic acid provided by the invention can be used to prepare 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde, And the yield of prepared 3-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde reaches 64.85%, and the purity measured by high performance liquid chromatography reaches at least 98.92%.

Main reference materials

[1] Preparation method of CN201610711939.83-(3-fluorobenzyl)-4-(3-fluorobenzyloxy)benzaldehyde

[2] CN201610711679.42-(3-bromo-4-(3-fluorobenzyloxy)phenyl)-1,3-dioxolane and preparation method thereof

[3] CN201610715421.12-(3-fluorobenzyloxy)-5-formylphenylboronic acid and preparation method thereof