Access to Highly Substituted 7-Azaindoles from 2-Fluoropyridines via 7-Azaindoline Intermediates.
A versatile synthesis of 7-azaindoles from substituted 2-fluoropyridines is described. C3-metalation and 1,4-addition to nitroolefins provide substituted 2-fluoro-3-(2-nitroethyl)pyridines. A facile oxidative Nef reaction/reductive amination/intramolecular SNAr sequence furnishes 7-azaindolines. Finally, optional regioselective electrophilic C5-substitution (e.g., bromination or nitration) and subsequent in situ oxidation delivers highly functionalized 7-azaindoles in high overall efficiency.
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Philippe
P
Nuhant
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Christophe
C
Allais
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Ming Z
MZ
Chen
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Jotham W
JW
Coe
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Alpay
A
Dermenci
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Olugbeminiyi O
OO
Fadeyi
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
Andrew C
AC
Flick
Worldwide Medicinal Chemistry, Pfizer Inc. , 445 Eastern Point Road, Groton, Connecticut 06340, United States.
James J
JJ
Mousseau