HCID 86722465, compound → HCID 86722467, compound

Participants

Reaction Steps

(E)-1-(4-Fluorophenyl)-5-(pyridin-2-ylmethylene)-5,7,8,9-tetrahydrocyclohepta[b]pyrazolo[4,3-e]pyridin-6(1H)-one (19.53 g, 50.8 mmol) (assumed 100% for previous reaction), in toluene (500 mL) with palladium hydroxide on carbon (20% wet) (1.784 g, 2.54 mmol) was stirred for about 22 h under an atmosphere of hydrogen provided by a balloon. The catalyst was removed by filtration through a pad of Celite® and the pad was washed with DCM (250 mL). The filtrate was concentrated under reduced pressure then the material was purified on silica gel (330 g) using a gradient from 0-100% EtOAc in DCM. Product fractions were combined and concentrated under reduced pressure to yield 1-(4-fluorophenyl)-5-(pyridin-2-ylmethyl)-5,7,8,9-tetrahydrocyclohepta[b]pyrazolo[4,3-e]pyridin-6(1H)-one (115, R1=4-Fluorophenyl, R2=Pyridin-2-ylmethyl) (16.47 g, 84%); LC/MS, method 3, Rt=1.97 min, MS m/z 387 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.47-8.46 (m, 1H), 8.34 (s, 1H), 8.33-8.26 (m, 2H), 8.09 (s, 1H), 7.72-7.68 (m, 1H), 7.46-7.34 (m, 3H), 7.23-7.17 (m, 1H), 5.00-4.97 (m, 1H), 3.88-3.82 (m, 1H), 3.72-3.65 (m, 1H), 3.36-3.29 (m, 1H), 3.25-3.19 (m, 1H), 3.07-2.99 (m, 1H), 2.54-2.48 (m, 1H), 2.33-2.25 (m, 1H), 1.80-1.69 (m, 1H).

Provenance & Evidence