Dimethylformamide → HCID 59389388, compound

Participants

Reaction Steps

Palladium acetate (101.8 mg) was dissolved in DMF (25 mL) in an argon atmosphere. To this solution, 1,3-bis(diphenylphosphino)propane (373.9 mg) was added and the mixture was stirred at room temperature for 15 min. Subsequently, the compound of Example 67 (4.25 g) in DMF (65 mL), ethyl-1-propenyl ether (15.0 mL) and triethylamine (3.8 mL) were added and the mixture was stirred at 80° C. for 20 hours. The reaction was terminated by adding water and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate, followed by evaporation of the solvent under reduced pressure. THF (50 mL) and 3 mol/L hydrochloric acid (50 mL) were added and the mixture was stirred at room temperature for 16 hours. Subsequently, the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=6:1) afforded the title compound as a yellow powder (670 mg).

Provenance & Evidence