4-bromo-2-chlorobenzenesulfonamide

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the product obtained in step 1 (1.0 g, 3.70 mmol) in ACN (8 ml) was added CuI (35 mg, 185 μmol), PdCl2(PPh3)2 (389 mg, 554 μmol) and 1-(ethoxyvinyl)tributyl-stannane (2.5 ml, 2.60 g, 7.39 mmol). The mixture was heated for 30 min at 100° C. using microwaves. After cooling, the reaction mixture was acidified with 1 N HCl (4 ml) and stirred for 20 min. The reaction mixture was adjusted to pH=7 using NaHCO3 and extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane (1:1) gave the desired product (650 mg, 75%). After cooling extracted with AcOEt The organic phase was washed with brine dried over Na2SO4 evaporated Purification of the crude product by silica gel chromatography

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the product obtained in step 1 (1.0 g, 3.70 mmol) in ACN (8 ml) was added CuI (35 mg, 185 μmol), PdCl2(PPh3)2 (389 mg, 554 μmol) and 1-(ethoxyvinyl)tributyl-stannane (2.5 ml, 2.60 g, 7.39 mmol). The mixture was heated for 30 min at 100° C. using microwaves. After cooling, the reaction mixture was acidified with 1 N HCl (4 ml) and stirred for 20 min. The reaction mixture was adjusted to pH=7 using NaHCO3 and extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane (1:1) gave the desired product (650 mg, 75%). After cooling extracted with AcOEt The organic phase was washed with brine dried over Na2SO4 evaporated Purification of the crude product by silica gel chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-bromo-2-chlorobenzenesulfonyl chloride (2.50 g, 8.45 mmol) in THF (25 ml) was added a solution of ammonia (25%, 6.3 ml, 84.5 mmol). The reaction mixture was stirred for 4 h at RT. Ethyl acetate (70 ml) and water (50 mL) were added. The organic phase was separated and washed with hydrochloric acid (1 M, 50 ml) and brine (2×30 ml) and dried over sodium sulfate. After evaporation the product was obtained as a white solid (2.05 g, 90%) which was used in the next step without further purification. The organic phase was separated washed with hydrochloric acid (1 M, 50 ml) and brine (2×30 ml) dried over sodium sulfate After evaporation the product

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to example 26b, reaction of 4-bromo-2-chloro-benzenesulfonamide (1.0 g, 3.7 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (271 mg, 0.37 mmol), (E)-3-cyclohexyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (1.5 g, 5.5 mmol) and aqueous sodium carbonat solution (2 M, 3.60 mL, 7.40 mmol) in 15 mL DMF at 80° C. and purification via column chromatography on silica gel, eluting with a gradient from 70:30 to 50:50 hexane:ethyl acetate affords the title compound as an oil (1.34 g). MS (m/e): 312 [(M−H2O)+H]. purification via column chromatography on silica gel eluting with a gradient from 70:30 to 50:50 hexane

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the product obtained in step 1 (1.0 g, 3.70 mmol) in ACN (8 ml) was added CuI (35 mg, 185 μmol), PdCl2(PPh3)2 (389 mg, 554 μmol) and 1-(ethoxyvinyl)tributyl-stannane (2.5 ml, 2.60 g, 7.39 mmol). The mixture was heated for 30 min at 100° C. using microwaves. After cooling, the reaction mixture was acidified with 1 N HCl (4 ml) and stirred for 20 min. The reaction mixture was adjusted to pH=7 using NaHCO3 and extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane (1:1) gave the desired product (650 mg, 75%). After cooling extracted with AcOEt The organic phase was washed with brine dried over Na2SO4 evaporated Purification of the crude product by silica gel chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-bromo-2-chlorobenzenesulfonyl chloride (2.50 g, 8.45 mmol) in THF (25 ml) was added a solution of ammonia (25%, 6.3 ml, 84.5 mmol). The reaction mixture was stirred for 4 h at RT. Ethyl acetate (70 ml) and water (50 mL) were added. The organic phase was separated and washed with hydrochloric acid (1 M, 50 ml) and brine (2×30 ml) and dried over sodium sulfate. After evaporation the product was obtained as a white solid (2.05 g, 90%) which was used in the next step without further purification. The organic phase was separated washed with hydrochloric acid (1 M, 50 ml) and brine (2×30 ml) dried over sodium sulfate After evaporation the product