1312312-78-9 | 1-Methyl-1H-pyrazolo[3,4-b]pyridine-5-boronic acid pinacol ester

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$63.00	$45.00
250mg	98%	in stock	$96.00	$68.00
500mg	98%	in stock	$152.00	$107.00
1g	98%	in stock	$227.00	$159.00

Description

• Catalog Number: AA40955
• Chemical Name: 1-Methyl-1H-pyrazolo[3,4-b]pyridine-5-boronic acid pinacol ester
• CAS Number: 1312312-78-9
• Molecular Formula: C13H18BN3O2
• Molecular Weight: 259.1119
• MDL Number: MFCD16995953
• SMILES: Cn1ncc2c1ncc(c2)B1OC(C(O1)(C)C)(C)C

Computed Properties

• Complexity: 348
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 19
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1

Upstream Synthesis Route

The synthesis of 1-Methyl-1H-pyrazolo[3,4-b]pyridine-5-boronic acid pinacol ester typically follows a multi-step synthetic pathway:

1. **Synthesis of the Pyrazolopyridine Core**:
The reaction generally begins with the formation of the pyrazolo[3,4-b]pyridine core, which can be synthesized through a cyclization reaction involving the appropriate hydrazine and a β-ketoester derivative followed by a cyclization step, often catalyzed under acidic conditions or via a cyclodehydration method.

2. **Methylation Step**:
Once the core is formed, a methylation step is generally carried out to introduce the methyl group at the appropriate position, usually using methylating agents like methyl iodide or dimethyl sulfate in the presence of a base such as potassium carbonate, under phase transfer catalysis conditions if necessary.

3. **Borylation**:
The borylation step involves introducing a boron group into the pyrazolopyridine core. This is typically achieved by transition metal-catalyzed C-H borylation using a boronic acid pinacol ester as the boron source in the presence of a suitable catalyst like a palladium or iridium complex, and often requires a directing group to ensure regioselectivity.

4. **Protection**
The boronic acid functional group is then protected by reacting with pinacol in a protection reaction to form the pinacol ester, ensuring stability of the boron-containing compound during work-up and purification.

5. **Purification**:
The final product is then purified using methods such as column chromatography, washing with suitable solvents, or recrystallization, depending on the specific requirements of the process and the by-products formed.

Each of these stages may need to be optimized depending on the starting materials' reactivity and the need for selectivity at each step. Safety procedures for handling potentially hazardous reagents must be followed, and the disposal of waste should be managed according to appropriate regulatory guidelines.