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

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Reaction Conditions

Reaction Steps

A mixture of 13-chloro-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6,12-triazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (1.60 g, 4.64 mmol), tributyl(1-ethoxyvinyl)stannane (1.70 g, 4.71 mmol), LiCl (585 mg, 13.9 mmol), and Pd(PPh3)4 (537 mg, 0.460 mmol) in THF (30 mL) in a sealed tube was stirred at 80° C. for 48 hrs under N2 atmosphere. After being cooled to room temperature, aq. KF (2.0 M, 50 mL) was added. 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 layers were washed brine and dried over MgSO4. Removal of the solvent gave the desired product (900 mg, 51% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.63 (s, 1H), 8.35 (s, 1H), 8.04 (s, 1H), 5.90 (m, 1H), 5.30 (s, 1H), 4.64-4.60 (m, 4H), 4.39 (s, 1H), 3.95-3.94 (m, 2H), 2.27 (s, 3H), 1.51-1.48 (m, 6H), 1.42-1.39 (m, 3H). LCMS m/z [M+H]+ 381.3

Provenance & Evidence