63725-51-9 | 6-Chloro-1H-pyrazolo[3,4-b]pyridine

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$15.00	$11.00
5g	95%	in stock	$60.00	$42.00
10g	95%	in stock	$116.00	$82.00
25g	95%	in stock	$266.00	$187.00
100g	95%	in stock	$997.00	$698.00

Description

• Catalog Number: AG76560
• Chemical Name: 6-Chloro-1H-pyrazolo[3,4-b]pyridine
• CAS Number: 63725-51-9
• Molecular Formula: C6H4ClN3
• Molecular Weight: 153.5691
• MDL Number: MFCD09832900
• SMILES: Clc1ccc2c(n1)[nH]nc2

Computed Properties

• Complexity: 130
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 1.8

Upstream Synthesis Route

The synthesis of 6-Chloro-1H-pyrazolo[3,4-b]pyridine typically involves a multistep procedure starting from readily accessible precursors such as 4-chloropyridine derivatives and hydrazines. A common synthetic approach is as follows:

1. **Hydrazinolysis**: Begin with a suitable 4-chloropyridine derivative such as 4-chloro-3-formylpyridine. This compound reacts with hydrazine hydrate to yield a pyridyl hydrazine intermediate.

2. **Cyclization**: Subject the pyridyl hydrazine to acidic conditions (e.g., polyphosphoric acid or another condensing agent) to induce cyclization, forming the pyrazolo[3,4-b]pyridine ring system. During this process, the hydrazine nitrogen atoms nucleophilically attack the formyl group to close the ring, resulting in the formation of a pyrazole moiety fused to the pyridine ring.

3. **Halogenation**: Once the pyrazolo[3,4-b]pyridine scaffold is in place, a chlorination step is conducted. If the starting material was not already chlorinated, various halogenating agents such as N-chlorosuccinimide (NCS), phosphorus oxychloride (POCl3), or thionyl chloride (SOCl2) can be used to introduce the chloro group at the desired position on the ring system.

4. **Purification**: After the construction of the core structure and introduction of the chlorine atom, standard purification techniques such as recrystallization or column chromatography are applied to isolate the pure 6-Chloro-1H-pyrazolo[3,4-b]pyridine.

5. **Characterization**: Verify the structure and purity of the final compound using NMR, IR, MS, and elemental analysis or HPLC.

Each step in the synthesis might require optimization based on the specific substrates and reagents used. It's also important to consider the regioselectivity of the halogenation step to ensure the chlorine is introduced at the correct position on the pyrazolo[3,4-b]pyridine ring.