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

Application of Selective Palladium??Mediated Functionalization of the Pyrido [3′, 2′: 4, 5] pyrrolo [1, 2??c] pyrimidine Heterocyclic System for the Total Synthesis of …

…, J Mendiola, C Burgos, J Alvarez??Builla…

Index: Mendiola, Javier; Baeza, Alejandro; Alvarez-Builla, Julio; Vaquero, Juan J. Journal of Organic Chemistry, 2004 , vol. 69, # 15 p. 4974 - 4983

Full Text: HTML

Citation Number: 11

Abstract

Abstract The reaction of protected 3-bromo-2-(bromomethyl)-4-methoxypyrrolo [2, 3-b] pyridine and tosylmethyl isocyanide (TosMIC) afforded a pyrido [3′, 2′: 4, 5] pyrrolo [1, 2- c] pyrimidine derivative in good yield. This compound was transformed through installation of the pyrimidine moiety in the C5 position, hydrolysis, and decarboxylation in an advanced intermediate for the total or formal synthesis of the naturalalkaloid variolin B. Reaction of 3 ...

7-Azaindole Structure

~%

methyl 3-bromo-2-methylpyrrolo[2,3-b]pyridine-1-carboxylate Structure

methyl 3-bromo-...

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

1-(Phenylsulfon...

~%

methyl 3-bromo-2-methylpyrrolo[2,3-b]pyridine-1-carboxylate Structure

methyl 3-bromo-...

2-METHYL-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE Structure

2-METHYL-1-(PHE...

~%

methyl 3-bromo-2-methylpyrrolo[2,3-b]pyridine-1-carboxylate Structure

methyl 3-bromo-...

Methyl chloroformate Structure

Methyl chloroformate

3-Bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine Structure

3-Bromo-4-chlor...

~79%

Methyl 3-bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine-1-carb oxylate Structure

Methyl 3-bromo-...

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

4-Chloro-1H-pyr...

~%

Methyl 3-bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine-1-carb oxylate Structure

Methyl 3-bromo-...

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

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

~%

Methyl 3-bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine-1-carb oxylate Structure

Methyl 3-bromo-...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-Methyl-1-(phenylsulfonyl)- Structure

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

~%

Methyl 3-bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine-1-carb oxylate Structure

Methyl 3-bromo-...

3-bromo-4-chloro-1-phenylsulfonyl-2-methylpyrrolo[2,3-b]pyridine Structure

3-bromo-4-chlor...

~%

Methyl 3-bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine-1-carb oxylate Structure

Methyl 3-bromo-...

3-bromo-4-chloro-1-phenylsulfonyl-2-methylpyrrolo[2,3-b]pyridine Structure

3-bromo-4-chlor...

~56%

3-Bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine Structure

3-Bromo-4-chlor...

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

4-Chloro-1H-pyr...

~%

3-Bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine Structure

3-Bromo-4-chlor...

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

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

~%

3-Bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine Structure

3-Bromo-4-chlor...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-Methyl-1-(phenylsulfonyl)- Structure

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

~%

3-Bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine Structure

3-Bromo-4-chlor...

methyl iodide Structure

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

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

~83%

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-Methyl-1-(phenylsulfonyl)- Structure

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

chlorophenylsulfone Structure

chlorophenylsulfone

~%

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-Methyl-1-(phenylsulfonyl)- Structure

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

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

4-Chloro-1H-pyr...

~%

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-Methyl-1-(phenylsulfonyl)- Structure

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

Methyl 3-bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine-1-carb oxylate Structure

Methyl 3-bromo-...

~63%

Methyl 3-bromo-2-(bromomethyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine -1-carboxylate Structure

Methyl 3-bromo-...

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

4-Chloro-1H-pyr...

~%

Methyl 3-bromo-2-(bromomethyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine -1-carboxylate Structure

Methyl 3-bromo-...

3-Bromo-4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine Structure

3-Bromo-4-chlor...

~%

Methyl 3-bromo-2-(bromomethyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine -1-carboxylate Structure

Methyl 3-bromo-...

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

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

~%

Methyl 3-bromo-2-(bromomethyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine -1-carboxylate Structure

Methyl 3-bromo-...

1H-Pyrrolo[2,3-b]pyridine, 4-chloro-2-Methyl-1-(phenylsulfonyl)- Structure

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

~%

Methyl 3-bromo-2-(bromomethyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine -1-carboxylate Structure

Methyl 3-bromo-...

3-bromo-4-chloro-1-phenylsulfonyl-2-methylpyrrolo[2,3-b]pyridine Structure

3-bromo-4-chlor...

~%

Methyl 3-bromo-2-(bromomethyl)-4-chloro-1H-pyrrolo[2,3-b]pyridine -1-carboxylate Structure

Methyl 3-bromo-...

4-Bromo-3,5-dimethylpyrazole Structure

4-Bromo-3,5-dim...

Methyl chloroformate Structure

Methyl chloroformate

~95%

1H-Pyrazole-1-carboxylicacid, 4-bromo-3,5-dimethyl-, methyl ester Structure

1H-Pyrazole-1-c...

chlorophenylsulfone Structure

chlorophenylsulfone

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

4-Chloro-1H-pyr...

~95%

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

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

methyl 3-bromo-2-methylpyrrolo[2,3-b]pyridine-1-carboxylate Structure

methyl 3-bromo-...

~91%

Methyl 3-bromo-2-(bromomethyl)-1H-pyrrolo[2,3-b]pyridine-1-carbox ylate Structure

Methyl 3-bromo-...

7-Azaindole Structure

~%

Methyl 3-bromo-2-(bromomethyl)-1H-pyrrolo[2,3-b]pyridine-1-carbox ylate Structure

Methyl 3-bromo-...

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

1-(Phenylsulfon...

~%

Methyl 3-bromo-2-(bromomethyl)-1H-pyrrolo[2,3-b]pyridine-1-carbox ylate Structure

Methyl 3-bromo-...

2-METHYL-1-(PHENYLSULFONYL)-1H-PYRROLO[2,3-B]PYRIDINE Structure

2-METHYL-1-(PHE...

~%

Methyl 3-bromo-2-(bromomethyl)-1H-pyrrolo[2,3-b]pyridine-1-carbox ylate Structure

Methyl 3-bromo-...