Triethylamine → Ethyl 3-[4-(1-methylpiperidin-4-ylidene)-9,10-dihydro-4H-3-thiabenzo[f]azulen-2-yl]acrylate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (35.5 mL, 255 mmol), ethyl acrylate (26.8 mL, 246 mmol), palladium acetate (0.4 g, 1.8 mmol), and tri(o-toluoyl)phosphine (1.5 g, 5.0 mmol) were added to a DMF (160 mL) solution of Compound 2 (9.2 g, 24.5 mmol), and the mixture was stirred overnight at 80° C. in an argon atmosphere. A saturated aqueous ammonium chloride solution was added to the reaction mixture, the product was extracted with ethyl acetate, and the organic layer was then washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the resulting residue was then purified by column chromatography (chloroform-methanol=9:1), to give 7.6 g (79%) of the captioned compound in the form of white crystals.

Provenance & Evidence