Methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate 98% Purity Brominated Heterocyclic Building Block Cross-Coupling and Drug Discovery Research Key

Product Overview

Methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate (CAS 1234616-07-9) is a high‑purity brominated fused heterocyclic building block featuring an imidazo[1,2‑b]pyridazine core with a bromine atom at the 3‑position and a methyl ester functionality at the 6‑position. The molecular formula is C₈H₆BrN₃O₂ with a molecular weight of 256.05 g/mol. The bromine atom at the 3‑position serves as a versatile handle for palladium‑catalyzed cross‑coupling reactions including Suzuki‑Miyaura, Buchwald‑Hartwig, and Sonogashira couplings, enabling the introduction of diverse substituents to build compound libraries. The methyl ester provides an orthogonal functional group for hydrolysis to the carboxylic acid, reduction to the alcohol, or conversion to amides. This compound is a valuable intermediate for the synthesis of kinase inhibitors and other biologically active molecules. Supplied at ≥98.0% purity.

Synthetic Process

The synthesis of methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate typically involves the bromination of the corresponding imidazopyridazine precursor. A representative synthetic route is described below:

• Step 1 – Construction of Imidazopyridazine Core: An appropriately substituted aminopyridazine derivative is condensed with an α‑halo carbonyl compound to form the imidazo[1,2‑b]pyridazine ring system.

• Step 2 – Bromination: The 3‑position is brominated using bromine or N‑bromosuccinimide (NBS) in a suitable solvent such as acetonitrile or dichloromethane under controlled conditions.

• Step 3 – Esterification (if required): The carboxylic acid intermediate is esterified with methanol in the presence of an acid catalyst.

• Step 4 – Purification: The crude product is purified by recrystallization or column chromatography to achieve ≥98% purity.

• Quality Control: The final product is rigorously characterized by HPLC, ¹H‑NMR, ¹³C‑NMR, and mass spectrometry.

Mechanism of Action

As a synthetic building block, methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate serves as a versatile precursor for:

• Kinase Inhibitor Synthesis: The imidazopyridazine core is widely utilized in kinase inhibitor development. The bromine atom at the 3‑position provides an entry point for introducing substituents that modulate potency and selectivity.

• C‑C and C‑N Bond Formation: The bromine atom enables palladium‑catalyzed cross‑coupling reactions, allowing the introduction of aryl, heteroaryl, amine, and alkyne substituents.

• Diverse Derivative Synthesis: The combination of the bromine atom and methyl ester allows for orthogonal derivatization, enabling the rapid generation of compound libraries with varied physicochemical properties.

Quality Specifications

Our Methyl 3-bromoimidazo[1,2-b]pyridazine-6-carboxylate is manufactured under strict quality control conditions: - Purity: ≥98.0% determined by HPLC - Identity confirmed by NMR and mass spectrometry - Water content: ≤0.5% - Residual solvents: Meet ICH Q3C guidelines - Each batch accompanied by comprehensive Certificate of Analysis (COA) - Stable for 24 months when stored at 2-8°C in sealed containers protected from light

Packaging & Shipping

We offer flexible packaging options to meet diverse customer needs: - Research quantities: 1g, 5g, 10g, 25g amber glass vials - Bulk quantities: 100g, 500g, 1kg amber glass bottles - Custom packaging available upon request - Shipped at ambient temperature for routine orders - International shipping available with proper documentation

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