Syntheses of novel 2,3-diaryl-substituted 5-cyano-4-azaindoles exhibiting c-Met inhibition activity.
Herein we report the syntheses of 2,3-diaryl-substituted pyrrolo[3,2-b]pyridine-5-carbonitriles via a one-pot 5-endo-dig-cyclization/protection reaction followed by palladium catalyzed arylation. In addition, a complementary synthesis route employing Larock methodology is applied to efficiently explore further aryl moieties in the 2-position. The novel compounds' expedient c-Met receptor tyrosine kinase inhibition activity is discussed.
Koolman
Hannes
H
Clemens-Schöpf Institute of Organic Chemistry and Biochemistry, Technical University of Darmstadt, Petersenstrasse 22, 64287 Darmstadt, Germany. hannes.koolman@merck.de
Heinrich
Timo
T
Böttcher
Henning
H
Rautenberg
Wilfried
W
Reggelin
Michael
M
D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D010165:Palladium / Q000737:chemistry; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019859:Proto-Oncogene Proteins c-met / Q000037:antagonists & inhibitors* / Q000378:metabolism
D007211:Indoles; D047428:Protein Kinase Inhibitors; D010165:Palladium; D019859:Proto-Oncogene Proteins c-met