ChemicalBook CAS DataBase List 3-Bromo-1,5-naphthyridine

3-Bromo-1,5-naphthyridine synthesis

9synthesis methods

Product Name:3-Bromo-1,5-naphthyridine
CAS Number:17965-71-8
Molecular formula:C8H5BrN2
Molecular Weight:209.04

254-79-5

17965-71-8

General procedure for the synthesis of 3-bromo-1,5-naphthyridine from 1,5-naphthyridine: To a 10 mL solution of glacial acetic acid containing compound 4 (2.7 g, 20.76 mmol) and NaOAc (3.41 g, 41.52 mmol), stirred at 85 °C, 1 M of bromine in acetic acid (35 mL) was slowly added, and the reaction lasted for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the acetic acid was removed by vacuum concentration. The product was purified by column chromatography (petroleum ether/ethyl acetate = 2:1) to give compound 5 (2.36 g, 55% yield) as a white solid. Melting point: 107-108 °C (literature value: 108-109 °C).1H NMR (400 MHz, CDCl3): δ 8.96 (d, J = 2.1 Hz, 2H), 8.56 (s, 1H), 8.36 (d, J = 8.5 Hz, 1H), 7.69-7.56 (m, 1H).

254-79-5 Synthesis

254-79-5
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$8.00/250mg

17965-71-8
131 suppliers
$27.00/100mg

Yield:17965-71-8 55%

Reaction Conditions:

with bromine;sodium acetate in acetic acid at 85; for 5 h;

Steps:

3-Bromo-1,5-naphthyridine (5)
3-Bromo-1,5-naphthyridine (5) To a stirring solutionof compound 4 (2.7 g, 20.76 mmol) and NaOAc(3.41 g,41.52 mmol) in 10 mL glacial AcOH at 85°C was added a solution of Br₂ (1 M) in AcOH (35 mL) for 5 h,then cooled to room temperature and concentrated in vacuum to remove AcOH.Purification by chromatography (PE/EA = 2:1) provided compound 5 (2.36 g, 55%) as a whitesolid. MP: 107~108°C (Ref.² 108~109°C).¹H NMR (400 MHz,CDCl₃): δ 8.96 (d, J = 2.1 Hz, 2H), 8.56 (s, 1H), 8.36 (d, J = 8.5 Hz, 1H), 7.69-7.56 (m, 1H).

References:

Wu, Jing-Fang;Liu, Ming-Ming;Huang, Shao-Xu;Wang, Yang [Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,# 16,art. no. 22772,p. 3251 - 3255] Location in patent:supporting information

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