885520-23-0 | 6-Bromo-4-fluoro-1H-indazole

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$16.00	$12.00
250mg	95%	in stock	$22.00	$16.00
1g	95%	in stock	$27.00	$19.00
5g	95%	in stock	$105.00	$73.00
100g	95%	in stock	$1,693.00	$1,185.00

Description

• Catalog Number: AB69731
• Chemical Name: 6-Bromo-4-fluoro-1H-indazole
• CAS Number: 885520-23-0
• Molecular Formula: C7H4BrFN2
• Molecular Weight: 215.0225
• MDL Number: MFCD07781444
• SMILES: Brc1cc(F)c2c(c1)[nH]nc2

Computed Properties

• Complexity: 155
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 2.3

Upstream Synthesis Route

To synthesize 6-Bromo-4-fluoro-1H-indazole, one would typically start with an ortho-fluoro-nitrobenzene derivative as the core structure to introduce the requisite halogen substituents through selective halogenation.

1. Begin with 3-fluoronitrobenzene as the starting material.
2. Subject it to a bromination reaction using a suitable brominating agent such as N-bromosuccinimide (NBS) in the presence of a radical initiator (e.g., AIBN) and a suitable solvent. Conduct the reaction under conditions that favor bromination at the para-position relative to the nitro group. This results in the formation of 3-fluoro-4-bromonitrobenzene.
3. Execute a palladium-catalyzed coupling (Suzuki coupling) using a boronic acid or ester derivative of an indazole, wherein the indazole component has a boronic acid functionality at the position where the nitrogen-containing heterocycle is to be fused. This step will link the brominated aromatic compound with the indazole system.
4. Apply a reducing agent to the nitro group to convert it into an amino group, using agents like iron powder in acidic media or using catalytic hydrogenation.
5. Last, induce cyclization to obtain the indazole core through intramolecular attack of the amine group on the fluoro-substituted phenyl entity with the loss of an HX molecule, under acidic conditions typically using polyphosphoric acid, thereby finalizing the synthesis of 6-Bromo-4-fluoro-1H-indazole.

This pathway ensures the establishment of both required halogen atoms on the aromatic system prior to the construction of the indazole core.