2096339-92-1 | 2,6-Bis(benzyloxy)pyridine-3-boronic acid

Packsize	Purity	Availability	Price	Discounted Price
250mg	98%	in stock	$22.00	$16.00
1g	98%	in stock	$58.00	$41.00
25g	98%	in stock	$775.00	$543.00

Description

• Catalog Number: AX55314
• Chemical Name: 2,6-Bis(benzyloxy)pyridine-3-boronic acid
• CAS Number: 2096339-92-1
• Molecular Formula: C19H18BNO4
• Molecular Weight: 335.1615
• MDL Number: MFCD18434424
• SMILES: OB(c1ccc(nc1OCc1ccccc1)OCc1ccccc1)O

Computed Properties

• Complexity: 372
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 25
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 7

Upstream Synthesis Route

To synthesize 2,6-Bis(benzyloxy)pyridine-3-boronic acid, the following upstream synthesis route can be employed:

1. Starting Material: Begin with 3-bromopyridine as the starting compound.

2. Oxyarylation: React 3-bromopyridine with phenol in the presence of a base such as potassium carbonate (K2CO3) to introduce the aryloxy groups at the 2 and 6 positions of the pyridine ring. This step typically involves a copper-catalyzed Ullmann-type coupling reaction.

3. Protection of Phenolic OH Groups: React the resulting 2,6-dihydroxypyridine with benzyl chloride and a base like potassium carbonate or sodium hydride (NaH) to protect the phenolic OH groups through benzylation. This yields 2,6-bis(benzyloxy)pyridine.

4. Borylation: Utilize a suitable borylation reagent, such as bis(pinacolato)diboron (B2pin2) in conjunction with a palladium catalyst, to introduce the boronic acid functionality at the 3-position of the pyridine ring. This step may also require a ligand such as SPhos and a base such as potassium acetate (KOAc) to facilitate the reaction.

5. Purification: Upon completion of the borylation reaction, purify the product to obtain 2,6-Bis(benzyloxy)pyridine-3-boronic acid using standard purification techniques such as column chromatography.

Each step should be monitored by NMR, GC-MS, or HPLC to ensure the desired transformations and purity of intermediates and final compound.