Lithium Chloride → HCID 86700380, compound

Participants

Reaction Conditions

Reaction Steps

In a 10 mL reaction vial, N-(2-bromo-6-(1-methyl-1H-indazol-5-yl)pyridin-3-yl)-2,2,2-trifluoroacetamide (24 mg, 0.06 mmol) was dissolved in dioxane (3 mL) at room temperature. The solution was bubbled with argon for 5 min. Then Sn2(n-Bu)6 (0.057 mL, 0.108 mmol), LiCl (30 mg, 0.7 mmol), Pd(PPh3)2Cl2 (6.3 mg, 0.009 mmol) and Pd(PPh3)4 (10 mg, 0.009 mmol) were added sequentially. The resulting reaction mixture was sealed and heated to 90° C. in oil bath. To this mixture, a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (44 mg, 0.09 mmol) in dioxane (1.5 mmol) was added slowly through syringe pump over 1.5 h. The resulting reaction mixture was stirred at 100° C. in oil bath for 16 h. The reaction was then diluted with EtOAc (20 mL) and filtered to remove solid. The filtrate was concentrated and purified on silica gel column with 0-20% EtOAc/Hex to afford product. LCMS-ESI+: calc'd for: C37H33ClF3N5O4S: 736.2, 737.2, 738.2 (M+H+); found: 736.1, 737.1, 738.1 (M+H+).

Provenance & Evidence