3-Chloro-2-fluorophenol → 2-[4-(3-chloro-2-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid

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In an analogous manner to the stepwise sequence outlined in Intermediate 70, starting from 5-iodo-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 70 step 2) and 3-chloro-2-fluoro-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 2-[4-(3-chloro-2-fluoro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid as a white solid (4.4 g, 73% for the final step); LC-MS: tR=4.80 min, 381 (M+H)+. HPLC: tR=8.83 min, 95.66% (214 nm), 95.56% (254 nm). 1H NMR (300 MHz, DMSO-d6): δ 13.06 (broad, 1H), 8.21 (d, 1H, J=2.7 Hz), 7.63-7.58 (m, 1H), 7.54-7.49 (m, 1H), 7.38-7.33 (m, 1H), 6.07 (d, 1H, J=2.7 Hz), 5.33 (dd, 1H, J=11.0 Hz, J=4.2 Hz), 2.40-2.10 (m, 1H), 1.99-1.90 (m, 1H), 1.68-1.43 (m, 7H), 1.13-1.04 (m, 2H).

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