The Production Process of 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionic acid methyl ester

2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionic acid methyl ester, also known as XY-506, is a research chemical used in neuroscience and neuropharmacology studies.
The production process of XY-506 involves several steps that require careful handling and purification to ensure the quality of the final product.
In this article, we will discuss the production process of XY-506 in detail, highlighting the key steps involved.

Step 1: Synthesis of 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide
The synthesis of 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide, the starting material for XY-506, involves a series of chemical reactions that require careful handling and purification.
The reaction sequence involves the following steps:

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Synthesis of N-[2-(5-ethyl-2-pyridyl)ethoxy]propanamide
In a typical synthesis, 5-ethyl-2-pyridinol is reacted with propanal in the presence of an acid catalyst, such as hydrochloric acid, to form N-[2-(5-ethyl-2-pyridyl)ethoxy]propanamide.

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Synthesis of N-[2-(5-ethyl-2-pyridyl)ethoxy]-3-bromopropanamide
N-[2-(5-ethyl-2-pyridyl)ethoxy]propanamide is then treated with hydrogen bromide in the presence of a solvent, such as acetonitrile, to form N-[2-(5-ethyl-2-pyridyl)ethoxy]-3-bromopropanamide.

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Synthesis of 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide
N-[2-(5-ethyl-2-pyridyl)ethoxy]-3-bromopropanamide is then reacted with 4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl acetate in the presence of a strong base, such as sodium hydroxide, to form 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide.

Step 2: Coupling of 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide with Methanol
The coupling of 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide with methanol is a two-step process that involves the following steps:

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Formation of Methyl 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionate
In the first step, 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionamide is treated with methanol and a strong acid, such as sulfuric acid, to form methyl 2-Bromo-3-[4-(2-(5-ethyl-2-pyridyl)ethoxy)phenyl]propionate.

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Dehydr