94220-45-8 | 5-Chloro-1H-pyrazolo[4,3-b]pyridine

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$6.00	$4.00
1g	97%	in stock	$9.00	$6.00
5g	95%	in stock	$36.00	$25.00
10g	95%	in stock	$68.00	$48.00
15g	95%	in stock	$102.00	$71.00
25g	95%	in stock	$166.00	$116.00
50g	95%	in stock	$327.00	$229.00

Description

• Catalog Number: AB48645
• Chemical Name: 5-Chloro-1H-pyrazolo[4,3-b]pyridine
• CAS Number: 94220-45-8
• Molecular Formula: C6H4ClN3
• Molecular Weight: 153.5691
• MDL Number: MFCD05663984
• SMILES: Clc1ccc2c(n1)cn[nH]2

Computed Properties

• Complexity: 130
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 1.5

Upstream Synthesis Route

The upstream synthesis route for 5-Chloro-1H-pyrazolo[4,3-b]pyridine involves several key steps, starting with the appropriate pyrazolone precursor:

1. Starting from 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, perform a Vilsmeier-Haack formylation to introduce a formyl group at the 4-position of the pyrazolone ring.

2. Convert the formyl group to a chloro group using hydrochloric acid and an appropriate chlorinating agent such as phosphorus oxychloride (POCl3) to produce 4-chloro-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one.

3. Next, conduct a nucleophilic substitution of the phenyl group by treating with hydrazine, which leads to cyclization, forming the intermediate pyrazolo[3,4-b]pyridine core.

4. Chlorinate the formed pyrazolo[3,4-b]pyridine at the appropriate position, often using POCl3 or N-chlorosuccinimide (NCS) as the chlorinating agent, to yield 5-Chloro-1H-pyrazolo[4,3-b]pyridine.

The reaction conditions such as temperature, solvents, and reaction times must be optimized for each step to ensure the highest yields and purity of the product. Additionally, workup procedures including purification steps, such as column chromatography or recrystallization, may be necessary to obtain 5-Chloro-1H-pyrazolo[4,3-b]pyridine in a form suitable for use in further synthetic applications.