Lithium Chloride → HCID 86700382, compound

Participants

Reaction Conditions

Reaction Steps

In a 10 mL reaction vial, 5-(4-bromo-1-methyl-1H-imidazol-2-yl)-1-methyl-1H-indazole (50 mg, 0.172 mmol) was dissolved in dioxane (3 mL) at rt. The solution was bubbled with argon for 5 min. Then Sn2(n-Bu)6 (0.136 mL, 0.259 mmol), LiCl (60 mg, 1.4 mmol), Pd(PPh3)2Cl2 (24 mg, 0.034 mmol) and Pd(PPh3)4 (40 mg, 0.0344 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 (128 mg, 0.259 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: C34H34ClN5O3S: 628.2, 629.2, 630.2 (M+H+); found: 628.1, 629.1, 630.1 (M+H+)

Provenance & Evidence