Methyl vinyl ketone → HCID 86722476, compound

Participants

Reaction Conditions

Reaction Steps

Sodium (2.21 g, 96 mmol) and EtOH (350 mL) were stirred until a solution was formed. 3-Methoxy-9-(pyridin-2-ylmethyl)-6,7-dihydro-5H-cyclohepta[c]pyridin-8 (9H)-one (128, R2=Pyridin-2-ylmethyl) (26.6 g, 94 mmol) was suspended in EtOH (220 mL) then treated with the sodium ethoxide solution. The mixture was warmed to an internal temperature of about 63° C. then but-3-en-2-one (9.76 mL, 118 mmol) was added over about 2 to 3 min. The mixture was stirred at an internal temperature of about 65-70° C. for about 45 min then the mixture was cooled to rt. The solvents were removed under reduced pressure then the material was stirred with EtOH (250 mL) for about 30 min. The solids were collected by filtration then washed with EtOH (25 mL). The material was dried to yield 3-methoxy-11a-(pyridin-2-ylmethyl)-6,7,11,11a-tetrahydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridin-9(10H)-one (129, R2=Pyridin-2-ylmethyl) (18.89 g, 60.0%); LC/MS, method 3, Rt=1.12, 1.82 min, MS m/z 335 (M+H)+. 1H NMR (400 MHz, DMSO) δ 8.44 (s, 1H), 8.42-8.37 (m, 1H), 7.63-7.58 (m, 1H), 7.18-7.14 (m, 1H), 7.13-7.08 (m, 1H), 6.58 (s, 1H), 5.88 (s, 1H), 3.83 (s, 3H), 3.70 (d, J=13.4 Hz, 1H), 3.56 (d, J=13.4 Hz, 1H), 2.87-2.75 (m, 1H), 2.74-2.59 (m, 2H), 2.41-2.05 (m, 4H), 1.85-1.65 (m, 3H).

Provenance & Evidence