HCID 86722474, compound → HCID 86722475, compound

Participants

Reaction Steps

(E)-3-Methoxy-9-(pyridin-2-ylmethylene)-6,7-dihydro-5H-cyclohepta[c]pyridin-8 (9H)-one (127, R5=Pyridin-2-yl) (36.15 g, 129 mmol) in toluene (800 mL) with 20 wt % (wet) palladium hydroxide on carbon (4.53 g, 6.45 mmol) was stirred under a hydrogen filled balloon for about 7 h. The catalyst was removed by filtration through a pad of Celite® then the pad was washed with toluene (250 mL). The filtrate was concentrated under reduced pressure then the material was purified on silica gel (330 g) using 100% EtOAc. Product fractions were combined and concentrated under reduced pressure to yield 3-methoxy-9-(pyridin-2-ylmethyl)-6,7-dihydro-5H-cyclohepta[c]pyridin-8(9H)-one (128, R2=Pyridin-2-ylmethyl) (26.64 g, 73%); LC/MS, method 3, Rt=1.14 min, MS m/z 283 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.48-8.43 (m, 1H), 7.79 (s, 1H), 7.71-7.64 (m, 1H), 7.29 (d, J=7.8 Hz, 1H), 7.20-7.17 (m, 1H), 6.68 (s, 1H), 4.69-4.60 (m, 1H), 3.78 (s, 3H), 3.74-3.68 (m, 1H), 3.25-3.06 (m, 2H), 2.92-2.78 (m, 2H), 2.49-2.43 (m, 1H), 2.15-2.01 (m, 1H), 1.75-1.57 (m, 1H).

Provenance & Evidence