16727-47-2 | 2,6-Bis(benzyloxy)-3-bromopyridine

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$15.00	$10.00
250mg	95%	in stock	$15.00	$11.00
5g	95%	in stock	$17.00	$12.00
10g	95%	in stock	$22.00	$16.00
25g	95%	in stock	$30.00	$21.00
100g	95%	in stock	$84.00	$59.00

Description

• Catalog Number: AA89548
• Chemical Name: 2,6-Bis(benzyloxy)-3-bromopyridine
• CAS Number: 16727-47-2
• Molecular Formula: C19H16BrNO2
• Molecular Weight: 370.2398
• MDL Number: MFCD18434484
• SMILES: Brc1ccc(nc1OCc1ccccc1)OCc1ccccc1

Computed Properties

• Complexity: 329
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 23
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• XLogP3: 5.1

Upstream Synthesis Route

The upstream synthesis route for 2,6-Bis(benzyloxy)-3-bromopyridine involves the following steps:

1. **Starting Material:** The process typically begins with 3-bromopyridine as the starting material due to the presence of the bromine functional group at the desired position on the pyridine ring, which enables further functionalization.

2. **O-Functionalization:** The hydroxy groups at the 2 and 6 positions on the pyridine ring must be introduced. This is achieved through the selective O-functionalization of the pyridine nucleus. One approach could be to use a protecting group strategy wherein the starting 3-bromopyridine could be converted into a 2,6-diol derivative followed by protection as a bis(benzyloxy) compound.

3. **Protection with Benzyl Groups:**
- **Diol Preparation:** Through a halogen-lithium exchange reaction, 2,6-lithiated intermediates are formed using n-BuLi or LDA as the lithium source. Then, electrophilic quenching with an appropriate oxidizing agent can furnish the 2,6-dihydroxypyridine.
- **Benzylation:** Once the diol is formed, a benzylation reaction is performed using benzyl chloride and a base, typically an amine like triethylamine (Et3N), to yield 2,6-bis(benzyloxy)pyridine. This step involves nucleophilic substitution of the hydroxyl groups with the benzyl protecting groups to mask them.

4. **Halogenation:** The appropriate 2,6-bis(benzyloxy)pyridine can then undergo selective bromination at the 3-position using a brominating agent such as N-bromosuccinimide (NBS) in the presence of a radical initiator like AIBN (azobisisobutyronitrile) if not already available from the initial step.

5. **Isolation and Purification:** The final step involves the isolation and purification of 2,6-Bis(benzyloxy)-3-bromopyridine, typically performed by column chromatography and confirmed by spectroscopic methods, such as NMR or mass spectrometry, to ensure the correct product structure and purity.

Please note that this proposed upstream synthesis could potentially vary based on required scales, desired purity, and cost considerations in an industrial setting. Safety considerations for handling pyridine derivatives, strong bases, and reactive halogenating agents must also be observed.