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

In search of simplicity and flexibility: A rational access to twelve fluoroindolecarboxylic acids

M Schlosser, A Ginanneschi…

Index: Schlosser, Manfred; Ginanneschi, Assunta; Leroux, Frederic European Journal of Organic Chemistry, 2006 , # 13 p. 2956 - 2969

Full Text: HTML

Citation Number: 21

Abstract

Abstract All twelve indolecarboxylic acids 1–12 carrying both a fluorine substituent and a carboxy group at the benzo ring have been prepared either directly from the corresponding fluoroindoles 13–16 or from the chlorinated derivatives 22, 23 and 25 by hydrogen/metal permutation (“metalation”), or from the bromo-or iodofluoroindoles 17–20 and 26, 27, 29 and 30 by halogen/metal permutation, the organometallic intermediate being each time ...

N/A Structure

~90%

6-Fluoro-4-iodo-1H-indole Structure

6-Fluoro-4-iodo...

6-fluoro-1-(triisopropylsilyl)-1H-indole Structure

6-fluoro-1-(tri...

~%

6-Fluoro-4-iodo-1H-indole Structure

6-Fluoro-4-iodo...

6-fluoroindole Structure

~%

6-Fluoro-4-iodo-1H-indole Structure

6-Fluoro-4-iodo...

4-Fluoro-2-nitrotoluene Structure

4-Fluoro-2-nitr...

~%

6-Fluoro-4-iodo-1H-indole Structure

6-Fluoro-4-iodo...

Carbon dioxide Structure

7-Bromo-5-fluoro-1H-indole Structure

7-Bromo-5-fluor...

~54%

5-fluoro-1H-indole-7-carboxylic acid Structure

5-fluoro-1H-ind...

5-Bromo-4-fluoro-1-(triisopropylsilyl)-1H-indole Structure

5-Bromo-4-fluor...

~87%

5-Bromo-4-fluoro-1H-indole Structure

5-Bromo-4-fluor...

4-Fluoro-1-(triisopropylsilyl)-1H-indole Structure

4-Fluoro-1-(tri...

~%

5-Bromo-4-fluoro-1H-indole Structure

5-Bromo-4-fluor...

1-Bromo-4-fluoro-2-nitrobenzene Structure

1-Bromo-4-fluor...

~%

5-Bromo-4-fluoro-1H-indole Structure

5-Bromo-4-fluor...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~%

5-Bromo-4-fluoro-1H-indole Structure

5-Bromo-4-fluor...

7-Bromo-4-fluoro-1H-indole Structure

7-Bromo-4-fluor...

~%

5-Bromo-4-fluoro-1H-indole Structure

5-Bromo-4-fluor...

4-Bromo-7-fluoro-1H-indole Structure

4-Bromo-7-fluor...

~74%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

tert-butyl 2-[(E)-2-chloroethenyl]-6-fluorophenylcarbamate Structure

tert-butyl 2-[(...

~37%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

tert-butyl 6-fluoro-2-[2-(trimethylsilyl)ethynyl]phenylcarbamate Structure

tert-butyl 6-fl...

~63%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

2-Fluoroaniline Structure

2-Fluoroaniline

~%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

tert-butyl (2-fluorophenyl)carbamate Structure

tert-butyl (2-f...

~%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

(2-fluoro-6-iodophenyl)carbamic acid tert-butyl ester Structure

(2-fluoro-6-iod...

~%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

(2-FLUORO-6-FORMYL-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER Structure

(2-FLUORO-6-FOR...

~%

7-Fluoro-1H-indole Structure

7-Fluoro-1H-indole

(4-Chloro-5-fluoroindol-1-yl)-tri(propan-2-yl)silane Structure

(4-Chloro-5-flu...

~92%

4-Chloro-5-fluoro-1H-indole Structure

4-Chloro-5-fluo...

4-Bromo-2-fluoronitrobenzene Structure

4-Bromo-2-fluor...

Vinylmagnesium bromide Structure

Vinylmagnesium ...

~34%

5-Bromo-7-fluoro-1H-indole Structure

5-Bromo-7-fluor...

1-Bromo-3-fluorobenzene Structure

1-Bromo-3-fluor...

~75%

2-Bromo-4-fluoro-1-nitrobenzene Structure

2-Bromo-4-fluor...

tert-butyl 2-[(E)-2-chloroethenyl]-4-fluorophenylcarbamate Structure

tert-butyl 2-[(...

~47%

5-Fluoroindole Structure

7-Bromo-5-fluoro-1H-indole Structure

7-Bromo-5-fluor...

~48%

5-Fluoroindole Structure

1-Bromo-3-fluorobenzene Structure

1-Bromo-3-fluor...

~%

5-Fluoroindole Structure

2-Bromo-4-fluoro-1-nitrobenzene Structure

2-Bromo-4-fluor...

~%

5-Fluoroindole Structure

4-FLUOROANILINE, N-BOC PROTECTED Structure

4-FLUOROANILINE...

~%

5-Fluoroindole Structure

tert-Butyl (4-fluoro-2-formylphenyl)carbamate Structure

tert-Butyl (4-f...

~%

5-Fluoroindole Structure

6-fluoroindole Structure

Carbon dioxide Structure

~59%

1H-INDOLE-7-CARBOXYLIC ACID, 6-FLUORO Structure

1H-INDOLE-7-CAR...

4-Fluoro-2-nitrotoluene Structure

4-Fluoro-2-nitr...

~%

1H-INDOLE-7-CARBOXYLIC ACID, 6-FLUORO Structure

1H-INDOLE-7-CAR...

2-Fluoroaniline Structure

2-Fluoroaniline

~%

(2-FLUORO-6-FORMYL-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER Structure

(2-FLUORO-6-FOR...

Di-tert-butyl dicarbonate Structure

Di-tert-butyl d...

~%

(2-FLUORO-6-FORMYL-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER Structure

(2-FLUORO-6-FOR...

5-Bromo-7-fluoro-1H-indole Structure

5-Bromo-7-fluor...

Carbon dioxide Structure

~56%

7-fluoro-1H-indole-5-carboxylic acid Structure

7-fluoro-1H-ind...

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~71%

1-Bromo-4-fluoro-2-nitrobenzene Structure

1-Bromo-4-fluor...

4-Fluoro-2-nitrotoluene Structure

4-Fluoro-2-nitr...

N,N-Dimethylformamide dimethyl acetal Structure

N,N-Dimethylfor...

~32%

6-fluoroindole Structure