2,6-Difluorophenol → 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid

Participants

Reaction Steps

In an analogous manner to the stepwise sequence outlined in intermediate 19, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 2,6-difluoro-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (13.2 g, 58%) as a white solid; ESI-MS 364 [M+H+]; HPLC: >98% (purity). 1H-NMR (300 MHz, CDCl3) δ 7.93-7.94 (d, 1H), 7.22-7.39 (m, 1H), 7.03-7.09 (m, 2H), 6.00 (s, 1H), 5.51-5.56 (m, 1H), 2.29-2.39 (m, 1H), 2.08-2.16 (m, 1H), 1.44-1.81 (m, 7H), 1.10-1.25 (m, 2H).

Provenance & Evidence