Recent Large-Scale Applications of Transition Metal-Catalyzed Couplings for the Synthesis of Pharmaceuticals - New Trends in Cross-Coupling: Theory and Applications - page 705

Carbonylation

Heck, carbonyl-
ation

Non-steroidal
anti-
inflammatory

CO 2 H

MeO

Ketoprofen Orudis

Oruvail

Heck,
carbonyl-
ation

28 Originally

developed by
Rh ˆ ne-Poulenc

Non-steroidal
anti-
inflammatory

1967 Generic

Heck Carbonylation

O

CO 2 H

Axitinib Inlyta Heck, Migita 29 Pfizer Vascular

endothelial
growth factor
(VEGF)
antagonist for
the treatment
of solid
tumors,
including
metastatic
renal cell
carcinoma

January 27,
2012

June 2020

Migita

O NHMe

N

S

Heck

N

N

Fexofenadine
hydro-
chloride

Allegra
Fexidine
Telfast
Fastofen
Tilfur
Vifas
Telfexo
Allerfexo

Sonogashira 30 (McGill

University)

Sanofi-Aventis
(originally
developed by
Sepracor in
1993)

Antihistamine
for the
treatment of
hay fever,
allergy
symptoms and
urticaria

July 1996 Generic

(February
2001)

CO 2 H

N

Ph
Ph

OH

￿HCl

OH