Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate

Base Information

• Chemical Name: Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate
• CAS No.: 335031-10-2
• Molecular Formula: C₁₀H₉BrN₂O₃
• Molecular Weight: 285.097
• DSSTox Substance ID: DTXSID90455545
• Mol file: 335031-10-2.mol

Synonyms:335031-10-2;METHYL 6-BROMO-2-OXO-1,2,3,4-TETRAHYDRO-1,8-NAPHTHYRIDINE-3-CARBOXYLATE;6-BROMO-1,2,3,4-TETRAHYDRO-2-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER;Methyl 6-bromo-2-oxo-3,4-dihydro-1H-1,8-naphthyridine-3-carboxylate;SCHEMBL726486;DTXSID90455545;AMY19167;MFCD08275095;AKOS016845682;PB29505;AS-38755;CS-0048943;FT-0645550;A821804;6-BROMO-2-OXO-1,2,3,4-TETRAHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID METHYL ESTER

Chemical Property of Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 438.965 °C at 760 mmHg
• PKA: 11.43±0.40(Predicted)
• Flash Point: 219.279 °C
• PSA: 68.29000
• Density: 1.622 g/cm³
• LogP: 1.26590
• Solubility.: DMSO, Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 283.97965
• Heavy Atom Count: 16
• Complexity: 310

Purity/Quality:

97% ^*data from raw suppliers

6-Bromo-1,2,3,4-tetrahydro-2-oxo-1,8-naphthyridine-3-carboxylicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC2=C(NC1=O)N=CC(=C2)Br
• Uses: Intermediate in the production of FabI inhibitors

Technology Process of Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate

There total 6 articles about Methyl 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

malonic acid dimethyl ester (108-59-8) + 2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide (335033-38-0) → 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylic acid methyl ester (335031-10-2)

Guidance literature:

malonic acid dimethyl ester; With sodium methylate; In methanol; at 20 ℃; for 0.75h;

2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide; In methanol; at 20 ℃;

Reference yield: 58.0%

malonic acid dimethyl ester (108-59-8) → 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylic acid methyl ester (335031-10-2) + 2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide (335033-38-0)

Guidance literature:

With sodium methylate; In methanol;

Reference yield:

(2-amino-3-pyridinyl)methanol (23612-57-9) → 6-bromo-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylic acid methyl ester (335031-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; bromine / 3 h / 20 - 35 °C

2: hydrogen bromide / water / 16 h / Reflux

3: sodium methylate / methanol / 16 h / 20 - 35 °C

With hydrogen bromide; bromine; sodium methylate; acetic acid; In methanol; water;

upstream raw materials:

malonic acid dimethyl ester

2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide

(2-amino-3-pyridinyl)methanol

2-aminopyridin-3-carboxylic acid

Downstream raw materials:

6-bromo-3,4-dihydro-1,8-naphthyridine-2(1H)-one

(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid

6-{(1E)-3-[4-hydroxy-4-phenylpiperidin-1-yl]-3-oxoprop-1-en-1-yl}-3,4-dihydro-1,8-naphthyridin-2(1H)-one

methyl 6-[(1E)-3-{4-[(4-fluorophenoxy)methyl]piperidin-1-yl}-3-oxoprop-1-en-1-yl]-2-oxo-1,2,3,4-tetrahydro-1,8-naphthyridine-3-carboxylate