Lithium Chloride → (S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(6-(1-methyl-1H-indazol-5-yl)pyridin-2-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

In a 10 mL reaction vial, (S)-ethyl 2-(2-bromo-5-methyl-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)-2-tert-butoxyacetate (50 mg, 0.0938 mmol) was dissolved in dry dioxane (1.5 mL) under argon atmosphere. The solution was bubbled with argon for 5 min. Then LiCl (11 mg, 0.256 mmol), CuI (5 mg, 0.026 mmol) and Pd(PPh3)4 (10 mg, 0.0085 mmol) were added sequentially. A solution of 1-methyl-5-(6-(tributylstannyl)pyridin-2-yl)-1H-indazole (43 mg, 0.0853 mmol) in 1.4-dioxane (1.5 mL) was then added drop-wise. The resulting reaction mixture was then sealed and heated in oil bath at 100° C. for 3 h. The resulting reaction mixture was diluted with EtOAc (5 mL), filtered and the filtrate was concentrated and purified on silica gel column with 0-40% EtOAc/Hex to afford the title product. LCMS-ESI+: calc'd for: C30H29F3N4O6S2: 663.2, 664.2 (M+H+); Found: 663.1, 664.3 (M+H+).

Provenance & Evidence