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

Synthesis and derivatization of 3-perfluoroalkyl-substituted 7-azaindoles

H Schirok, S Figueroa-Pérez, M Thutewohl…

Index: Schirok, Hartmut; Figueroa-Perez, Santiago; Thutewohl, Michael; Paulsen, Holger; Kroh, Walter; Klewer, Dagmar Synthesis, 2007 , # 2 p. 251 - 258

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Citation Number: 7

Abstract

Originally, we began the synthesis with 2,6-dichloropyridine (1a in Scheme [2] ). Later on we found it advantageous to use 2-fluoropyridine (1b) as the starting material. The addition of trifluoroacetic acid ethyl ester to the lithiated pyridines and aqueous work-up yielded the hydrates 5a and 5b instead of the acetyl compounds, consistent with reports which describe the formation of stable gem-diols of 3-trifluoroacetylpyridine. [10] The dehydration can be achieved by azeotropic ...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

3-(Trifluoromet...

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide Structure

3-(Trifluoromet...

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

4-Nitro-3-(Trifluoromethyl)-7-Azaindole-7-Oxide Structure

4-Nitro-3-(Trif...

~%

1H-Pyrrolo[2,3-b]pyridine, 6-chloro-4-nitro-3-(trifluoromethyl)-1-[[2-(triMethylsilyl)ethoxy]Methyl]- Structure

1H-Pyrrolo[2,3-...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

~%

4-Nitro-3-(Trifluoromethyl)-7-Azaindole-7-Oxide Structure

4-Nitro-3-(Trif...

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

~%

4-Nitro-3-(Trifluoromethyl)-7-Azaindole-7-Oxide Structure

4-Nitro-3-(Trif...

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

3-(Trifluoromet...

~%

4-Nitro-3-(Trifluoromethyl)-7-Azaindole-7-Oxide Structure

4-Nitro-3-(Trif...

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

~%

4-Nitro-3-(Trifluoromethyl)-7-Azaindole-7-Oxide Structure

4-Nitro-3-(Trif...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

4-Nitro-3-(Trifluoromethyl)-7-Azaindole-7-Oxide Structure

4-Nitro-3-(Trif...

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide Structure

3-(Trifluoromet...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide Structure

3-(Trifluoromet...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide Structure

3-(Trifluoromet...

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide Structure

3-(Trifluoromet...

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

3-(Trifluoromet...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

3-(Trifluoromet...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

~%

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

3-(Trifluoromet...

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

~79%

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

~%

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

nitromethane Structure

~%

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

2,2,2-trifluoro-1-(2-fluoropyridin-3-yl)ethane-1,1-diol Structure

2,2,2-trifluoro...

~%

6-chloro-4-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

6-chloro-4-nitr...

1,1,1-Trifluoro-2-(2-Fluoropyridin-3-Yl)-3-Nitropropan-2-Ol Structure

1,1,1-Trifluoro...

~%

6-chloro-4-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

6-chloro-4-nitr...

2-Fluoropyridine Structure

2-Fluoropyridine

~%

6-chloro-4-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

6-chloro-4-nitr...

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

3-(Trifluoromet...

~%

6-chloro-4-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

6-chloro-4-nitr...

3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide Structure

3-(Trifluoromet...

~%

6-chloro-4-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

6-chloro-4-nitr...

1H-Pyrrolo[2,3-b]pyridin-3-ol, 2,3-dihydro-3-(trifluoroMethyl)- Structure

1H-Pyrrolo[2,3-...

~%

6-chloro-4-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine Structure

6-chloro-4-nitr...

Improved Synthesis of the Selective Rho-Kinase Inhibitor 6-C...

[Schirok, Hartmut; Paulsen, Holger; Kroh, Walter; Chen, Gang; Gao, Ping Organic Process Research and Development, 2010 , vol. 14, # 1 p. 168 - 173]