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

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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-phenyl-propionic acid methyl ester (Intermediate 13) afforded 2-[4-(2,6-difluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-phenyl-propionic acid as a white solid (555.8 mg, 96% for the final step); ES+-HRMS m/e calcd for C19H14N2O4F2 [M+H+] 373.0995, found 373.0994. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.28-3.37 (m, 1H), 3.44 (dd, J=14.3, 4.7 Hz, 1H), 5.64 (dd, J=11.1, 4.7 Hz, 1H), 5.96 (d, J=2.7 Hz, 1H), 7.09-7.25 (m, 5H), 7.30-7.41 (m, 2H), 7.41-7.52 (m, 1H), 8.19 (d, J=2.7 Hz, 1H), 13.24 (br s, 1H).

Provenance & Evidence