7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one: A Fused Heterocyclic Pharmaceutical Intermediate

Product Overview

7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one is a brominated fused heterocyclic compound used as a building block in pharmaceutical and medicinal chemistry research.

Its molecular structure contains a pyridine ring fused with an oxazinone ring, forming a bicyclic heteroaromatic framework. The molecule also incorporates a bromine substituent, which provides an opportunity for further chemical functionalization.

The combination of a rigid fused-ring structure, nitrogen and oxygen heteroatoms, and an aromatic bromine position makes this compound valuable for developing more complex heterocyclic molecules.

Product Specifications

• · Product Name: 7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one
• · CAS Number: 105544-36-3
• · Molecular Formula: C₇H₅BrN₂O₂
• · Molecular Weight: 229.03 g/mol
• · Chemical Class: Brominated fused pyrido-oxazinone
• · Synonyms: 7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2-one; 7-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-2-one

The molecular formula and molecular weight are supported by chemical reference data.

Structural Features and Synthetic Value

The synthetic value of this compound comes from its combination of a fused bicyclic scaffold and a bromine-containing functionalization site.

1. Fused Pyridine-Oxazinone Framework

The pyrido[2,3-b][1,4]oxazinone core contains both nitrogen and oxygen atoms within a fused ring system.

This framework provides a defined molecular geometry and multiple heteroatom interaction sites. Such structural characteristics are relevant to medicinal chemistry programs that explore heterocyclic scaffolds for biological activity.

The oxazinone carbonyl group also distinguishes this compound from its corresponding reduced oxazine analogs.

2. Bromine as a Functionalization Handle

The bromine atom at the 7-position provides an important site for further molecular modification.

Under suitable conditions, the carbon-bromine bond may participate in palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura coupling.

These transformations can introduce additional aromatic or heteroaromatic fragments while retaining the fused heterocyclic core.

3. Oxazinone Carbonyl Functionality

The carbonyl group is an important structural feature of the oxazinone ring.

It influences the compound’s electronic properties, hydrogen-bonding behavior, and chemical reactivity.

When selecting this material for downstream synthesis, buyers should distinguish it from the corresponding dihydro-oxazine compound, which does not contain the same carbonyl functionality.

Reported Synthetic Preparation

Published chemical reference information describes a preparation of 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one involving a brominated pyrrolopyridine starting material and a carbonochloridate reagent.

The reported procedure uses pyridine and cyclohexyl carbonochloridate in anhydrous THF, followed by reaction work-up and chromatographic purification.

The reported laboratory preparation provides useful reference information for understanding the compound’s synthetic accessibility. However, the exact route and process conditions used by an individual commercial supplier should be confirmed independently.

Potential Applications in Pharmaceutical Research

Brominated fused heterocycles are useful in medicinal chemistry because they allow researchers to modify specific positions of a pre-existing molecular scaffold.

For CAS 105544-36-3, potential research and synthesis applications include:

• · Preparation of substituted pyrido-oxazinone derivatives
• · Palladium-catalyzed cross-coupling studies
• · Development of fused nitrogen-containing heterocycles
• · Pharmaceutical intermediate research
• · Heterocyclic compound library development
• · Structure-activity relationship studies

The compound is also listed in the supplied product portfolio in connection with Necrostatin-2-related sourcing. However, its exact role in a commercial Necrostatin-2 manufacturing route should be verified against the relevant process documentation before being described as an established API intermediate.

Quality Control Considerations

For pharmaceutical buyers, quality evaluation should focus on structural identity, assay, and impurities associated with the synthesis and purification process.

The distinction between oxazinone and oxazine structures is particularly important. These compounds differ in molecular formula, molecular weight, and functional-group composition, so analytical methods should be capable of identifying the correct structure.

What B2B Buyers Should Confirm Before Procurement

When evaluating CAS 105544-36-3, procurement teams should request sufficient technical information to establish the material’s suitability for the intended synthesis.

Important questions include:

1. Is the product identity confirmed by NMR and mass spectrometry?

2. What HPLC assay specification is available?

3. Which related substances are routinely monitored?

4. Can a representative batch COA be provided?

5. Is sample material available for downstream reaction evaluation?

6. What packaging and storage conditions are recommended?

7. Can customized purity or impurity specifications be supported?

These details are especially relevant when the material is used in multi-step pharmaceutical intermediate synthesis.

Pharmaceutical Intermediate Capabilities at Shanghai Lizhuo

Shanghai Lizhuo Pharmaceutical Technology Co., Ltd. focuses on pharmaceutical intermediate R&D, custom synthesis, and production support.

According to its company profile, the company operates a 1,000 m² R&D laboratory and two pilot production workshops in Wuhan. Its technical equipment includes reactors ranging from 50 L to 1,000 L, temperature-control systems, and facilities for different chemical process requirements.

For customers evaluating CAS 105544-36-3, relevant cooperation areas may include specification confirmation, sample evaluation, custom synthesis, and batch-quality coordination.

Further information is available through the official company profile.

Conclusion

7-Bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one is a brominated fused heterocyclic building block with a defined pyridine-oxazinone framework.

Its aromatic bromine atom provides opportunities for downstream functionalization, while the oxazinone carbonyl group establishes an important structural distinction from reduced oxazine analogs.

For pharmaceutical procurement, the key considerations are verified molecular identity, controlled related substances, reliable analytical documentation, and consistent batch quality.