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

Tetrahedron letters

Synthesis of functionalized 7-azaindoles via directed ortho-metalations

A L'Heureux, C Thibault, R Ruel

Index: L'Heureux, Alexandre; Thibault, Carl; Ruel, Rejean Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2317 - 2319

Full Text: HTML

Citation Number: 24

Abstract

7-Azaindole derivatives may be considered as useful indole bioisosteres in medicinal chemistry and functionalization at C-2 and C-3 of the 7-azaindole ring system is well described in the scientific literature. Substitution of the pyrrole ring has been effected either directly on the 7-azaindole core or, alternatively, by cyclization of a requisite pyridine precursor. 1 On the other hand, the limited number of examples of 4-, 5-, and 6-substituted 7-azaindoles reported thus far ...

4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-OL Structure

4-CHLORO-1-(TRI...

~49%

1-(Triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol Structure

1-(Triisopropyl...

Chloro(triisopropyl)silane Structure

Chloro(triisopr...

~%

1-(Triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol Structure

1-(Triisopropyl...

4-Chloro-1H-pyrrolo[2,3-b]pyridine Structure

4-Chloro-1H-pyr...

~%

1-(Triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol Structure

1-(Triisopropyl...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]- Structure

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

~%

1-(Triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol Structure

1-(Triisopropyl...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]- Structure

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

~47%

(4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-YL)BORONIC ACID Structure

(4-CHLORO-1-(TR...

Chloro(triisopropyl)silane Structure

Chloro(triisopr...

~%

(4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-YL)BORONIC ACID Structure

(4-CHLORO-1-(TR...

4-Chloro-1H-pyrrolo[2,3-b]pyridine Structure

4-Chloro-1H-pyr...

~%

(4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-YL)BORONIC ACID Structure

(4-CHLORO-1-(TR...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]- Structure

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

~66%

4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-OL Structure

4-CHLORO-1-(TRI...

Chloro(triisopropyl)silane Structure

Chloro(triisopr...

~%

4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-OL Structure

4-CHLORO-1-(TRI...

4-Chloro-1H-pyrrolo[2,3-b]pyridine Structure

4-Chloro-1H-pyr...

~%

4-CHLORO-1-(TRIISOPROPYLSILYL)-1H-PYRROLO[2,3-B]PYRIDIN-5-OL Structure

4-CHLORO-1-(TRI...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]- Structure

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

~67%

4-Chloro-5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine Structure

4-Chloro-5-fluo...

4-Fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine Structure

4-Fluoro-1-(tri...

~%

1H-Pyrrolo[2,3-b]pyridin-5-amine, 4-fluoro-1-[tris(1-methylethyl)silyl]- Structure

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

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]- Structure

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

~79%

(5-bromo-4-chloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Structure

(5-bromo-4-chlo...

4-Chloro-1H-pyrrolo[2,3-b]pyridine Structure

4-Chloro-1H-pyr...

~%

(5-bromo-4-chloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Structure

(5-bromo-4-chlo...

Chloro(triisopropyl)silane Structure

Chloro(triisopr...

~%

(5-bromo-4-chloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Structure

(5-bromo-4-chlo...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[tris(1-methylethyl)silyl]- Structure

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

~86%

(5-azido-4-chloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Structure

(5-azido-4-chlo...

Chloro(triisopropyl)silane Structure

Chloro(triisopr...

~%

(5-azido-4-chloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Structure

(5-azido-4-chlo...

4-Chloro-1H-pyrrolo[2,3-b]pyridine Structure

4-Chloro-1H-pyr...

~%

(5-azido-4-chloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane Structure

(5-azido-4-chlo...

4-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE 7-OXIDE Structure

4-CHLORO-1H-PYR...

~58%

4,6-Dichloro-1H-pyrrolo[2,3-b]pyridine Structure

4,6-Dichloro-1H...

1-(Triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-ol Structure

1-(Triisopropyl...

~72%

5-Hydroxy-7-azaindole Structure

5-Hydroxy-7-aza...