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2-[4-chloro-3-(4-cyano-2,6-dimethyl-phenoxy)-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate; In hexane;
EXAMPLE 3 2-[4-Chloro-3-(4-cyano-2,6-dimethyl-phenoxy)-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-55) step 1-A solution of 40 (0.600 g, 2.79 mmol), <strong>[867367-02-0]3,5-dimethyl4-fluorobenzonitrile</strong> (41, 0.459 g, 3.07 mmol), K2CO3 (1.157 g, 8.37 mmol) and NMP (6 mL) was stirred and heated to 120 C. for 6 h. When the starting material was consumed the solution was cooled and acidified with 10% HCl and twice extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography and eluted with an EtOAc/hexane gradient (100% hexane to 50% hexane) to afford 106a. Steps 2-4 were carried out as described in steps 7-9 of Example 1 which afforded I-55. Compound I-56 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-methyl-benzenesulfonamide. Compound I-68 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 2-chloroaniline. Compound I-135 was prepared using a similar procedure except in step 4, 4-amino-benzenesulfonamide was replaced with 4-amino-2-chloro-benzenesulfonamide.
With potassium carbonate; In N-methylpyrrolidone (NMP); at 120℃; for 6h;
A solution of 40 (0.600 g, 2.79 mmol), <strong>[867367-02-0]3,5-dimethyl-4-fluorobenzonitrile</strong> (41, 0.459 g, 3.07 mmol), K2CO3 (1.157 g, 8.37 mmol) and NMP (6 mL) was stirred and heated to 120 C. for 6 h. When the starting material was consumed the solution was cooled and acidified with 10% HCl and twice extracted with EtOAc. The combined extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography and eluted with an EtOAc/hexane gradient (100% hexane to 50% hexane) to afford 106a.
With C44H59F3NO5PPdS; cesium fluoride; In toluene; at 130℃; for 12h;Inert atmosphere;
General procedure: In a nitrogen filled glovebox an oven-dried resealable tube equipped with a stir bar was charged with (in this order) CsF (2.0 mmol, 2.0 eq.), OTf-tBuBrettPhos precatalyst (1-5%), aryl triflate (1.0 mmol, 1.0 eq.), and toluene (5 mL). The tube was sealed with a Teflon septum and removed from the glovebox, and the reaction mixture was stirred at 120-130 C. overnight. The reaction mixture was then allowed to cool to room temperature, filtered through celite eluting with Et2O, and concentrated via rotary evaporation. The crude product was purified by flash chromatography. See FIG. 18.
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