A Facile Two-Step Synthesis of 3-Fluoro-6-methoxyquinoline

B Li, Z Zhang, M Mangano

Index: Hoeglund, Iisa P. J.; Silver, Satu; Engstroem, Mia T.; Salo, Harri; Tauber, Andrei; Kyyroenen, Hanna-Kaisa; Saarenketo, Pauli; Hoffren, Anna-Marja; Kokko, Kurt; Pohjanoksa, Katariina; Sallinen, Jukka; Savola, Juha-Matti; Wurster, Siegfried; Kallatsa, Oili A. Journal of Medicinal Chemistry, 2006 , vol. 49, # 21 p. 6351 - 6363

Full Text: HTML

Citation Number: 2

Abstract

... American Chemical Society. * To whom correspondence should be addressed. Fax: 1(860)715-1448. E-mail: bryan.li@pfizer.com. ... cold storage. figure Scheme 1. We considered the functionalization of chloroquinolines. Heteroaromatic ...

 Related Synthetic Route
2-[(4-Nitrophenyl)amino]ethanol Structure

1965-54-4

2-[(4-Nitrophen...

~%

N,N-diethyl-N-(4-nitrophenyl)ethane-1,2-diamine Structure

5464-09-5

N,N-diethyl-N-(...

2-((4-nitrophenyl)amino)ethyl methanesulfonate Structure

100418-51-7

2-((4-nitrophen...

Diethylamine Structure

109-89-7

Diethylamine

~%

N,N-diethyl-N-(4-nitrophenyl)ethane-1,2-diamine Structure

5464-09-5

N,N-diethyl-N-(...

Triethyl orthoacetate Structure

78-39-7

Triethyl orthoa...

Diethyl malonate Structure

105-53-3

Diethyl malonate

~67%

Diethyl 2-(1-ethoxyethylidene)malonate Structure

3044-06-2

Diethyl 2-(1-et...

2-methyl-acetoacetic acid-ethylester-anil Structure

461666-14-8

2-methyl-acetoa...

~%

4-Quinolinol,2,3-dimethyl- Structure

10352-60-0

4-Quinolinol,2,...

Ethyl 2-methylacetoacetate Structure

609-14-3

Ethyl 2-methyla...

~%

4-Quinolinol,2,3-dimethyl- Structure

10352-60-0

4-Quinolinol,2,...

Structure

74497-02-2

~%

4-Quinolinol,2,3-dimethyl- Structure

10352-60-0

4-Quinolinol,2,...

4-Chloronitrobenzene Structure

100-00-5

4-Chloronitrobenzene

~%

N,N-diethyl-N-(4-nitrophenyl)ethane-1,2-diamine Structure

5464-09-5

N,N-diethyl-N-(...

Diethyl 2-(1-ethoxyethylidene)malonate Structure

3044-06-2

Diethyl 2-(1-et...

~%

4-HYDROXY-2-METHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Structure

73987-39-0

4-HYDROXY-2-MET...

Diethyl malonate Structure

105-53-3

Diethyl malonate

~%

4-HYDROXY-2-METHYL-QUINOLINE-3-CARBOXYLIC ACID ETHYL ESTER Structure

73987-39-0

4-HYDROXY-2-MET...

Ethyl 2-methylacetoacetate Structure

609-14-3

Ethyl 2-methyla...

~%

2,3,8-TRIMETHYLQUINOLIN-4-OL Structure

1203-47-0

2,3,8-TRIMETHYL...

o-Toluidine Structure

95-53-4

o-Toluidine

~%

2,3,8-TRIMETHYLQUINOLIN-4-OL Structure

1203-47-0

2,3,8-TRIMETHYL...

N/A Structure

139579-84-3

N/A

~%

2H-Pyrido[1,2-a]pyrazin-1(6H)-one,hexahydro-(6CI,8CI,9CI) Structure

15932-71-5

2H-Pyrido[1,2-a...

Ethyl pipecolinate Structure

15862-72-3

Ethyl pipecolinate

~%

2H-Pyrido[1,2-a]pyrazin-1(6H)-one,hexahydro-(6CI,8CI,9CI) Structure

15932-71-5

2H-Pyrido[1,2-a...

Ethyl acetoacetate Structure

141-97-9

Ethyl acetoacetate

Triethyl orthoacetate Structure

78-39-7

Triethyl orthoa...

~29%

ethyl 2-acetyl-3-ethoxybut-2-enoate Structure

99181-91-6

ethyl 2-acetyl-...

N/A Structure

791785-57-4

N/A

~%

1-(4-Chloro-2-methyl-3-quinolinyl)-ethanone Structure

138770-67-9

1-(4-Chloro-2-m...

ethyl 2-acetyl-3-ethoxybut-2-enoate Structure

99181-91-6

ethyl 2-acetyl-...

~%

1-(4-Chloro-2-methyl-3-quinolinyl)-ethanone Structure

138770-67-9

1-(4-Chloro-2-m...

Structure

74497-02-2

~%

1-(4-Chloro-2-methyl-3-quinolinyl)-ethanone Structure

138770-67-9

1-(4-Chloro-2-m...

2,3,8-TRIMETHYLQUINOLIN-4-OL Structure

1203-47-0

2,3,8-TRIMETHYL...

~%

4-chloro-2,3,8-trimethylquinoline Structure

1203-45-8

4-chloro-2,3,8-...

Ethyl 2-methylacetoacetate Structure

609-14-3

Ethyl 2-methyla...

~%

4-chloro-2,3,8-trimethylquinoline Structure

1203-45-8

4-chloro-2,3,8-...

o-Toluidine Structure

95-53-4

o-Toluidine

~%

4-chloro-2,3,8-trimethylquinoline Structure

1203-45-8

4-chloro-2,3,8-...

Pyrrolidine Structure

123-75-1

Pyrrolidine

2-((4-nitrophenyl)amino)ethyl methanesulfonate Structure

100418-51-7

2-((4-nitrophen...

~86%

4-nitro-N-(2-pyrrolidin-1-ylethyl)aniline Structure

863453-76-3

4-nitro-N-(2-py...

2-[(4-Nitrophenyl)amino]ethanol Structure

1965-54-4

2-[(4-Nitrophen...

~%

4-nitro-N-(2-pyrrolidin-1-ylethyl)aniline Structure

863453-76-3

4-nitro-N-(2-py...

4-Chloronitrobenzene Structure

100-00-5

4-Chloronitrobenzene

~%

4-nitro-N-(2-pyrrolidin-1-ylethyl)aniline Structure

863453-76-3

4-nitro-N-(2-py...

Homopiperazine Structure

505-66-8

Homopiperazine

~%

4-(4-Methyl-1,4-diazepan-1-yl)aniline Structure

219132-82-8

4-(4-Methyl-1,4...

1-Bromo-4-nitrobenzene Structure

586-78-7

1-Bromo-4-nitro...

~%

4-(4-Methyl-1,4-diazepan-1-yl)aniline Structure

219132-82-8

4-(4-Methyl-1,4...

2-((4-nitrophenyl)amino)ethyl methanesulfonate Structure

100418-51-7

2-((4-nitrophen...

~%

4-N-(2-pyrrolidin-1-ylethyl)benzene-1,4-diamine Structure

863453-84-3

4-N-(2-pyrrolid...

2-[(4-Nitrophenyl)amino]ethanol Structure

1965-54-4

2-[(4-Nitrophen...

~%

4-N-(2-pyrrolidin-1-ylethyl)benzene-1,4-diamine Structure

863453-84-3

4-N-(2-pyrrolid...

4-Chloronitrobenzene Structure

100-00-5

4-Chloronitrobenzene

~%

4-N-(2-pyrrolidin-1-ylethyl)benzene-1,4-diamine Structure

863453-84-3

4-N-(2-pyrrolid...

diethyl 2-(1-(phenylamino)ethylidene)malonate Structure

81022-80-2

diethyl 2-(1-(p...

~%

ethyl 4-chloro-2-methylquinoline-3-carboxylate Structure

50593-70-9

ethyl 4-chloro-...

Diethyl 2-(1-ethoxyethylidene)malonate Structure

3044-06-2

Diethyl 2-(1-et...

~%

ethyl 4-chloro-2-methylquinoline-3-carboxylate Structure

50593-70-9

ethyl 4-chloro-...

Diethyl malonate Structure

105-53-3

Diethyl malonate

~%

ethyl 4-chloro-2-methylquinoline-3-carboxylate Structure

50593-70-9

ethyl 4-chloro-...

Ethyl 3-oxo-4-phenylbutanoate Structure

5413-05-8

Ethyl 3-oxo-4-p...

~%

2-methyl-3-phenyl-1H-quinolin-4-one Structure

5350-61-8

2-methyl-3-phen...

Structure

74497-02-2

~%

2-methyl-3-phenyl-1H-quinolin-4-one Structure

5350-61-8

2-methyl-3-phen...

Ethyl 4-hydroxyquinoline-3-carboxylate Structure

26892-90-0

Ethyl 4-hydroxy...

~93%

Ethyl 4-chloro-3-quinolinecarboxylate Structure

13720-94-0

Ethyl 4-chloro-...

3-METHYLQUINOLIN-4-OL Structure

64965-46-4

3-METHYLQUINOLI...

~85%

4-Chloro-3-methylquinoline Structure

63136-60-7

4-Chloro-3-meth...

4-Chloronitrobenzene Structure

100-00-5

4-Chloronitrobenzene

2-Methyl-1,2-propanediamine Structure

811-93-8

2-Methyl-1,2-pr...

~88%

2-Methyl-N1-(4-nitrophenyl)-1,2-propanediamine Structure

440102-93-2

2-Methyl-N1-(4-...

2H-Pyrido[1,2-a]pyrazin-1(6H)-one,hexahydro-(6CI,8CI,9CI) Structure

15932-71-5

2H-Pyrido[1,2-a...

~%

Octahydro-1H-pyrido[1,2-a]pyrazine Structure

4430-75-5

Octahydro-1H-py...

N/A Structure

139579-84-3

N/A

~%

Octahydro-1H-pyrido[1,2-a]pyrazine Structure

4430-75-5

Octahydro-1H-py...

Ethyl pipecolinate Structure

15862-72-3

Ethyl pipecolinate

~%

Octahydro-1H-pyrido[1,2-a]pyrazine Structure

4430-75-5

Octahydro-1H-py...

ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE Structure

219949-95-8

ETHYL 4-HYDROXY...

~%

3-METHYLQUINOLIN-4-OL Structure

64965-46-4

3-METHYLQUINOLI...

2-methyl-3-(phenylimino)succinic acid diethyl ester Structure

408532-32-1

2-methyl-3-(phe...

~%

3-METHYLQUINOLIN-4-OL Structure

64965-46-4

3-METHYLQUINOLI...

Structure

74497-02-2

~%

3-METHYLQUINOLIN-4-OL Structure

64965-46-4

3-METHYLQUINOLI...

Homopiperazine Structure

505-66-8

Homopiperazine

~%

1-methyl-4-(4-nitrophenyl)-1,4-diazepane Structure

223786-22-9

1-methyl-4-(4-n...

1-Bromo-4-nitrobenzene Structure

586-78-7

1-Bromo-4-nitro...

~%

1-methyl-4-(4-nitrophenyl)-1,4-diazepane Structure

223786-22-9

1-methyl-4-(4-n...

4-Quinolinol,2,3-dimethyl- Structure

10352-60-0

4-Quinolinol,2,...

~%

Quinoline, 4-chloro-2,3-dimethyl- Structure

63136-62-9

Quinoline, 4-ch...

Ethyl 2-methylacetoacetate Structure

609-14-3

Ethyl 2-methyla...

~%

Quinoline, 4-chloro-2,3-dimethyl- Structure

63136-62-9

Quinoline, 4-ch...

2-methyl-acetoacetic acid-ethylester-anil Structure

461666-14-8

2-methyl-acetoa...

~%

Quinoline, 4-chloro-2,3-dimethyl- Structure

63136-62-9

Quinoline, 4-ch...

Structure

74497-02-2

~%

Quinoline, 4-chloro-2,3-dimethyl- Structure

63136-62-9

Quinoline, 4-ch...

ethyl ethoxalylpropionate Structure

759-65-9

ethyl ethoxalyl...

~%

ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE Structure

219949-95-8

ETHYL 4-HYDROXY...

2-methyl-3-(phenylimino)succinic acid diethyl ester Structure

408532-32-1

2-methyl-3-(phe...

~%

ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE Structure

219949-95-8

ETHYL 4-HYDROXY...

Structure

74497-02-2

~%

ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE Structure

219949-95-8

ETHYL 4-HYDROXY...

ethyl ethoxalylpropionate Structure

759-65-9

ethyl ethoxalyl...

~%

ethyl 4-chloro-3-methylquinoline-2-carboxylate Structure

24782-23-8

ethyl 4-chloro-...

2-methyl-3-(phenylimino)succinic acid diethyl ester Structure

408532-32-1

2-methyl-3-(phe...

~%

ethyl 4-chloro-3-methylquinoline-2-carboxylate Structure

24782-23-8

ethyl 4-chloro-...

ETHYL 4-HYDROXY-3-METHYLQUINOLINE-2-CARBOXYLATE Structure

219949-95-8

ETHYL 4-HYDROXY...

~%

ethyl 4-chloro-3-methylquinoline-2-carboxylate Structure

24782-23-8

ethyl 4-chloro-...

Structure

74497-02-2

~%

ethyl 4-chloro-3-methylquinoline-2-carboxylate Structure

24782-23-8

ethyl 4-chloro-...


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