HCID 68093065, compound → HCID 66685692, compound

Participants

Reaction Steps

Methyl 8-[2((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylate (Intermediate 5, 0.147 g) was suspended in ethanol. Formic acid (2 drops) was added and the flask was evacuated and purged with nitrogen gas. Palladium hydroxide (20% wt, 0.015 g) was added and nitrogen was replaced by hydrogen and the mixture was stirred at room temperature under an atmosphere of hydrogen for 1 hour. The mixture was filtered through a pad of Celite and washed with ethanol. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 2.5-10% to give methyl 8-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4,5-dihydro-3,6-dioxabenzo[e]azulene-7-carboxylate (0.134 g) as a yellow glassy solid.

Provenance & Evidence