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With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 16.0h;
(1-5) (846 mg, 2.68 mmol), (1-6) (815 mg, 3.21 mmol), [1,1'-bis(diphenylphosphino)-ferrocene) dichloropalladium (108 mg, 0.133 mmol), and KOAc (893 mg, 9.10 mmol) were combined in DMSO (10 mL, purged with N2 for 10 minutes) and then the solution was warmed to 80 C. After 16 h, the solution was filtered through Celite and then H2O (50 mL) and EtOAc (50 mL) was added. The organic phase was extracted and dried (Na2SO4), concentrated, and then passed through a silica plug with 50% EtOAc/Hexane. The solvent was concentrated to afford 1.22 g of crude (1-7) used directly in the next step.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80.0℃; for 16.0h;
(1-5) (846 mg, 2.68 mmol), (1-6) (815 mg, 3.21 mmol), [1,1'-bis(diphenylphosphino)-ferrocene)dichloropalladium (108 mg, 0.133 mmol), and KOAc (893 mg, 9.10 mmol) were combined in DMSO (10 ml, purged with N2 for 10 minutes) and then the solution was warmed to 80C. After 16 h, the solution was filtered through Celite and then H20 (50 mL) and EtOAc (50 mL) was added. The organic phase was extracted and dried (Na2SO4), concentrated, and then passed through a silica plug with 50% EtOAc/Hexane. The solvent was concentrated to afford 1.22 g of crude (1-7) used directly in the next step.
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 80.0℃; for 16.0h;
The boronic ester (1-7) (4144 mg, 11.4 mmol), (1-8) (2890 mg, 7.60 mmol), dichlorobis(triphenylphosphine)palladium(II) (534 mg, 0.760 mmol), DME (40 mL, De-gassed for 30 minutes with N2), and 1N Na2CO3 (40 mL, De-gassed for 30 minutes with N2) were combined and heated to 80 C. After 16 h, the reaction was cooled to rt and EtOAc (80 mL) was added. The solution was filtered through celite and then water (80 mL) was added. The organic layer was separated, dried (Na2SO4), and concentrated. The product was purified by flash chromatography to afford 1486 mg of (1-9) as a tan solid (36%).
36%
With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; at 80.0℃; for 16.0h;
The boronic ester (1-7) (4144 mg, 11.4 mmol), (1-8) (2890 mg, 7.60 mmol), dichlorobis(triphenylphosphine)palladium(ll) (534 mg, 0.760 mmol), DME (40 mL, De-gassed for 30 minutes with N2), and 1N Na2CO3 (40 mL, De-gassed for 30 minutes with N2) were combined and heated to 80C. After 16 h, the reaction was cooled to rt and EtOAc (80 mL) was added. The solution was filtered through celite and then water (80 mL) was added. The organic layer was separated, dried (Na2SO4), and concentrated. The product was purified by flash chromatography to afford 1486 mg of th 9) as a tan solid (36 %).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 105.0℃; for 17.0h;Inert atmosphere;
General procedure: Under nitrogen, DMSO (12 mL) was added to a solution of 4-iodo-N- (2- (methylsulfonyl) ethyl) amine (78 mg,0.24 mmol),Pinacol ester (75mg, 0.30mmol) with boronic acid,Potassium acetate (75 mg, 0.76 mmol)Pd (dppf) Cl2 (9 mg, 0.01 mmol)105 C for 17 h, the reaction solution was cooled to room temperature, extracted with ethyl acetate (50 mL x 3)The organic phase was concentrated and chromatographed (petroleum ether / ethyl acetate (v / v) = 1/2) to give 58 mg of a colorless oil, yield:74.4%.
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