e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A facile synthesis of 7-halo-5H-indeno [1, 2-b] pyridines and-pyridin-5-ones

MT DuPriest, CL Schmidt, D Kuzmich…

Index: DuPriest, Mark T.; Schmidt, Charles L.; Kuzmich, Daniel; Williams, Stanly B Journal of Organic Chemistry, 1986 , vol. 51, # 11 p. 2021 - 2023

Full Text: HTML

Citation Number: 39

Abstract

The 2-aryl-3-methylpyridines 7a-c were obtained in good yield by the addition of the corresponding aryllithium to 2-fluoro-3-methylpyridine. Permanganate oxidation provided the 2-aryl-3-pyridinecarboxylic acids 8a-c which were cyclized to 5H-indeno [l, 2-b] pyridin-5- ones 6a-c in hot polyphosphoric acid. The 5H-indeno [1, 2-b] pyridines 5a-c were readily obtained from the ketones 6a-c by treatment with hydrazine in hot diethylene glycol.

2-(4-fluorophenyl)-3-methylpyridine Structure

2-(4-fluorophen...

~59%

2-(4-FLUOROPHENYL)NICOTINIC ACID Structure

2-(4-FLUOROPHEN...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

~%

2-(4-FLUOROPHENYL)NICOTINIC ACID Structure

2-(4-FLUOROPHEN...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~%

2-(4-FLUOROPHENYL)NICOTINIC ACID Structure

2-(4-FLUOROPHEN...

7-fluoro-5H-indeno[1,2-b]pyridin-5-one Structure

7-fluoro-5H-ind...

~80%

7-fluoro-5H-indeno[1,2-b]pyridine Structure

7-fluoro-5H-ind...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

~%

7-fluoro-5H-indeno[1,2-b]pyridine Structure

7-fluoro-5H-ind...

2-(4-fluorophenyl)-3-methylpyridine Structure

2-(4-fluorophen...

~%

7-fluoro-5H-indeno[1,2-b]pyridine Structure

7-fluoro-5H-ind...

2-(4-FLUOROPHENYL)NICOTINIC ACID Structure

2-(4-FLUOROPHEN...

~%

7-fluoro-5H-indeno[1,2-b]pyridine Structure

7-fluoro-5H-ind...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~%

7-fluoro-5H-indeno[1,2-b]pyridine Structure

7-fluoro-5H-ind...

2-Phenylnicotinic acid Structure

2-Phenylnicotin...

~98%

5H-Indeno(1,2-b)pyridin-5-one Structure

5H-Indeno(1,2-b...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

~%

5H-Indeno(1,2-b)pyridin-5-one Structure

5H-Indeno(1,2-b...

Phenyllithium Structure

~%

5H-Indeno(1,2-b)pyridin-5-one Structure

5H-Indeno(1,2-b...

3-Methyl-2-phenylpyridine Structure

3-Methyl-2-phen...

~62%

2-Phenylnicotinic acid Structure

2-Phenylnicotin...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~%

2-(4-fluorophenyl)-3-methylpyridine Structure

2-(4-fluorophen...

2-(4-chlorophenyl)pyridine-3-carboxylic acid Structure

2-(4-chlorophen...

~84%

7-chloro-5H-Indeno[1,2-b]pyridin-5-one Structure

7-chloro-5H-Ind...

4-Bromochlorobenzene Structure

4-Bromochlorobenzene

~%

7-chloro-5H-Indeno[1,2-b]pyridin-5-one Structure

7-chloro-5H-Ind...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

~%

7-chloro-5H-Indeno[1,2-b]pyridin-5-one Structure

7-chloro-5H-Ind...

2-(4-chlorophenyl)-3-methylpyridine Structure

2-(4-chlorophen...

~%

7-chloro-5H-Indeno[1,2-b]pyridin-5-one Structure

7-chloro-5H-Ind...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

Phenyllithium Structure

~80%

3-Methyl-2-phenylpyridine Structure

3-Methyl-2-phen...

3-Methyl-2-phenylpyridine Structure

3-Methyl-2-phen...

~%

5H-Indeno[1,2-b]pyridine Structure

5H-Indeno[1,2-b...

2-Phenylnicotinic acid Structure

2-Phenylnicotin...

~%

5H-Indeno[1,2-b]pyridine Structure

5H-Indeno[1,2-b...

2-Fluoro-3-methylpyridine Structure

2-Fluoro-3-meth...

~%

5H-Indeno[1,2-b]pyridine Structure

5H-Indeno[1,2-b...

Phenyllithium Structure

~%

5H-Indeno[1,2-b]pyridine Structure

5H-Indeno[1,2-b...