Tetrahydrofuran → 3-{9-[8-(2,2,2-Trifluoro-acetyl)-8-aza-bicyclo[3.2.1]oct-3-ylidene]-9H-xanthen-3-yl}-4H-[1,2,4]thiadiazol-5-one

Participants

Reaction Steps

A mixture of compound 6a (0.0417 g, 0.094 mmol) and TCDI (0.025 g, 0.14 mmol) in THF (2 mL) was stirred at room temperature for 45 min. The mixture was diluted with H2O (2 mL) and extracted with EtOAc (3×5 mL). The combined organic extracts were washed with H2O (15 mL), dried (MgSO4), and concentrated. The residue was dissolved in THF (2 mL). Boron trifluoride diethyl etherate was added to the solution, and the resulting mixture was stirred at room temperature for 1 h. The mixture was diluted with H2O (2 mL) and extracted with EtOAc (3×5mL). The organic layers were dried (MgSO4), and concentrated. The resultant compound 9a was used in the next reaction without further purification. MS m/z (MH+) 485.8.

Provenance & Evidence