HCID 53465552, compound → HCID 136000178, compound

Participants

Reaction Steps

Pd/C (1 g) was added to a solution of Intermediate 3B, 4-(3-(4-(benzyloxy)phenyl)-1-(2-fluoroethyl)-1H-pyrazol-4-yl)pyridine (2.1 g) in EtOAc/EtOH (30 mL+30 mL). The mixture was stirred in autoclave at 2.5 atm H2 for 18 h. Pd/C was filtered off and the filtrate was concentrated under reduced pressure to yield the crude product. Purification by flash column chromatography afforded the pure product, 4-(1-(2-fluoroethyl)-4-(pyridin-4-yl)-1H-pyrazol-3-yl)phenol (1.46 g, 92%). 1H NMR (300 MHz, methanol-d4) δ 8.37 (dd, J=4.6, 1.6, 2H), 8.08 (s, 1H), 7.31 (dd, J=4.6, 1.7, 2H), 7.27-7.22 (m, 2H), 6.83-6.78 (m, 2H), 4.81 (dt, J=47.1, 4.7, 2H), 4.49 (dt, J=26.6, 4.7, 2H). MS (DCI—NH3) m/z=284 (M+H)+. (Note: Alternative preparation experimental details published in Journal of Medicinal Chemistry 2011, 54, 5820-5835, Compound 8b)

Provenance & Evidence