Beilstein J. Org. Chem.2018,14, 786–795, doi:10.3762/bjoc.14.66
highly efficient route for the synthesis of axitinib.
Keywords: axitinib; ball-milling; dehalogenation; Heck reaction; indazoles; Introduction
The palladium-catalyzed vinylation of alkenes in the presence of a base, known as the Heck reaction (Mizoroki–Heck reaction), is one of the most important
[33][34] and axitinib [35][36][37][38] (Scheme 1).
Mechanochemistry as a burgeoning technique to promote solvent-free reactions has led to remarkable advances [39][40][41][42], particularly for cross-coupling reactions [43][44][45], involving Heck coupling with the aid of stoichiometric amounts of
broad utility of this method, a concise synthesis of axitinib, eutherapeutic drug for the treatment of renal cell carcinoma, was undertaken (Scheme 6). The reaction started from commercially available 6-bromo-1H-indazole (5), bromination of the 3-position and N-protection gave 3,6-dibromo-1-(tetrahydro