title: A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid.
abstract: A practical synthesis of a key pharmaceutical intermediate, 2-[(1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino]-5-fluoronicotinic acid (1), is described. To introduce the aminomethyl moiety of 2 via a palladium-catalyzed cyanation/reduction sequence, a regioselective chlorination of 7-azaindole via the N-oxide was developed. A highly selective monodechlorination of 2,6-dichloro-5-fluoronicotinic acid was discovered to afford the nicotinic acid 3. The two building blocks 2 and 3 were then coupled to complete the preparation of 1.
authors: Chemical Process R & D, Amgen Inc., One Amgen Center Drive, Thousand Oaks, California 91320-1799, USA. xinw@amgen.com
authors: Xin
authors: X
authors: Wang
authors: Ben
authors: B
authors: Zhi
authors: Jean
authors: J
authors: Baum
authors: Ying
authors: Y
authors: Chen
authors: Richard
authors: R
authors: Crockett
authors: Liang
authors: L
authors: Huang
authors: Shawn
authors: S
authors: Eisenberg
authors: John
authors: J
authors: Ng
authors: Robert
authors: R
authors: Larsen
authors: Mike
authors: M
authors: Martinelli
authors: Paul
authors: P
authors: Reider