65515-32-4 | Methyl 6-chloro-2-methoxypyridine-3-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$12.00	$8.00
250mg	98%	in stock	$22.00	$15.00
1g	98%	in stock	$31.00	$22.00
5g	98%	in stock	$129.00	$91.00
10g	98%	in stock	$233.00	$163.00
25g	98%	in stock	$449.00	$315.00

Description

• Catalog Number: AD13335
• Chemical Name: Methyl 6-chloro-2-methoxypyridine-3-carboxylate
• CAS Number: 65515-32-4
• Molecular Formula: C8H8ClNO3
• Molecular Weight: 201.607
• MDL Number: MFCD15142741
• SMILES: COC(=O)c1ccc(nc1OC)Cl

Computed Properties

• Complexity: 188
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• XLogP3: 2

Upstream Synthesis Route

To synthesize Methyl 6-chloro-2-methoxypyridine-3-carboxylate, one potential upstream synthetic route is as follows:

1. **Starting Material:** We begin with methyl acetoacetate which will serve as the building block for the pyridine ring.

2. **Formation of Enamine**: Methyl acetoacetate can be treated with an amine, such as ammonia or a primary amine under mild conditions, to form a corresponding enamine.

3. **Condensation with Alkylating Agent**: The enamine can undergo an aldol-like condensation with an appropriate α-halo carbonyl compound, such as chloroacetone, in the presence of a base, to produce the substituted pyridine ring. The reaction may proceed via intermolecular cyclization of the enamine with the activated methylene group in α-position relative to the carbonyl group of the chloroacetone.

4. **Cyclization**: The intermediate imine formed from the condensation then undergoes intramolecular cyclization with the loss of water, typically aided by an acid catalyst, to form the pyridine ring.

5. **Halogenation**: Introduce the chlorine atom at position 6 of the pyridine ring. This can be done through a halogenation reaction, such as free radical chlorination, using a reagent like N-chlorosuccinimide (NCS) under appropriate conditions.

6. **O-Methylation**: Finally, to introduce the methoxy group at the 2-position, an O-methylation step can be carried out using dimethyl sulfate or methyl iodide in the presence of a base like potassium carbonate.

7. **Purification**: The crude product would then typically be purified through methods such as recrystallization or column chromatography to yield the pure Methyl 6-chloro-2-methoxypyridine-3-carboxylate.

Please note that each step must be followed by purification of intermediates, and the reaction conditions require careful control and optimization to yield the desired product with good purity and yield. Safety considerations, especially while handling hazardous reagents and during the chlorination step, must be of highest priority.