Lithium Chloride → 13-(1-Ethoxyethenyl)-12-methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene

Participants

Reaction Conditions

Reaction Steps

A mixture of 13-bromo-12-methyl-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (1.50 g, 3.73 mmol), tributyl(1-ethoxyvinyl)stannane (1.35 g, 3.74 mmol), LiCl (472 mg, 11.2 mmol), Pd(PPh3)4 (130 mg, 0.120 mmol) in THF (30 mL) was stirred at 80° C. for 16 hrs under N2 atmosphere in a sealed tube. After being cooled to room temperature, the mixture was treated with aq. KF (2.0 M, 50.0 mL). The resulting mixture was stirred at room temperature for 1 h and then filtered. The filtrate was extracted with ethyl acetate (5×50 mL). The combined organic layer was washed with brine and dried over MgSO4. Removal of the solvent gave the crude product (2.0 g, over 100% yield) as pale yellow oil, which was used directly in the next step without further purification. LCMS m/z [M+H]+ 395.3.

Provenance & Evidence