Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics

Thomas Flagstad; Mette Terp Petersen; Daniel Michael Hinnerfeldt; Michael Christian Givskov; Thomas Eiland Nielsen

doi:10.1055/s-0034-1378554

Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics

Thomas Flagstad, Mette Terp Petersen, Daniel Michael Hinnerfeldt, Michael Christian Givskov, Thomas Eiland Nielsen

Department of Chemistry

University of Copenhagen

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81-85%. Halogenated quinoline building blocks have found much use in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds. © Georg Thieme Verlag.

Original language	English
Journal	Synthesis
Volume	46
Issue number	26
Pages (from-to)	3263–3267
ISSN	0039-7881
DOIs	https://doi.org/10.1055/s-0034-1378554
Publication status	Published - 2014

Keywords

Catalysis
Organic Chemistry
antibiotic
fluorine
heterocycle
quinolone
regioselectivity

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title = "Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics",

abstract = "A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81-85%. Halogenated quinoline building blocks have found much use in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds. {\textcopyright} Georg Thieme Verlag.",

keywords = "Catalysis, Organic Chemistry, antibiotic, fluorine, heterocycle, quinolone, regioselectivity",

author = "Thomas Flagstad and Petersen, {Mette Terp} and Hinnerfeldt, {Daniel Michael} and Givskov, {Michael Christian} and Nielsen, {Thomas Eiland}",

year = "2014",

doi = "10.1055/s-0034-1378554",

language = "English",

volume = "46",

pages = "3263–3267",

journal = "Synthesis",

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TY - JOUR

T1 - Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics

AU - Flagstad, Thomas

AU - Petersen, Mette Terp

AU - Hinnerfeldt, Daniel Michael

AU - Givskov, Michael Christian

AU - Nielsen, Thomas Eiland

PY - 2014

Y1 - 2014

N2 - A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81-85%. Halogenated quinoline building blocks have found much use in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds. © Georg Thieme Verlag.

AB - A practical and scalable 4-step route is presented for the synthesis of 4-bromo-3-fluoro-6-methoxyoquinoline and 3-fluoro-4-iodo-6-methoxyoquinoline from readily available 2,4-dichloro-3-fluoroquinoline with an overall yield of 81-85%. Halogenated quinoline building blocks have found much use in antimicrobial drug discovery, and the method reported here would be useful for the synthesis of these compounds. © Georg Thieme Verlag.

KW - Catalysis

KW - Organic Chemistry

KW - antibiotic

KW - fluorine

KW - heterocycle

KW - quinolone

KW - regioselectivity

U2 - 10.1055/s-0034-1378554

DO - 10.1055/s-0034-1378554

M3 - Journal article

SN - 0039-7881

VL - 46

SP - 3263

EP - 3267

JO - Synthesis

JF - Synthesis

IS - 26

ER -

Synthesis of 4-Halogenated 3-Fluoro-6-methoxyquinolines: Key Building Blocks for the Synthesis of Antibiotics

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Keywords

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