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With potassium acetate In N,N-dimethyl-formamide at 90℃; for 2 h; Inert atmosphere
Step 2: Methyl 3-(4.4.5.5-tetramethyl-1.3,2-dioxaborolan-2-ylV5-(trifluoromethyl)benzoate (P42)A solution of compound P42a (2.51 g, 8.90 mmol), B2Pin2 (2.71 g, 10.7 mmol), AcOK (1.75 g, 17.8 mmol) and Pd(dppf)CI2 (300 mg) in dry DMF (40 mL) was heated at 90°C for 2 h under N2. The mixture was quenched with water and extracted with EA. The combined organic layers were washed with water and brine consecutively, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 50/1) to give compound P42 (2.11 g, 72percent) as a white solid.
3-bromo-5-trifluoromethylbenzoic acid methyl ester[ No CAS ]
[ 73183-34-3 ]
[ 1150271-61-6 ]
Yield
Reaction Conditions
Operation in experiment
72%
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 90.0℃; for 2.0h;Inert atmosphere;
Step 2: Methyl 3-(4.4.5.5-tetramethyl-1.3,2-dioxaborolan-2-ylV5-(trifluoromethyl)benzoate (P42)A solution of compound P42a (2.51 g, 8.90 mmol), B2Pin2 (2.71 g, 10.7 mmol), AcOK (1.75 g, 17.8 mmol) and Pd(dppf)CI2 (300 mg) in dry DMF (40 mL) was heated at 90C for 2 h under N2. The mixture was quenched with water and extracted with EA. The combined organic layers were washed with water and brine consecutively, dried over Na2S04, filtered, concentrated and purified by CC (PE/EA = 50/1) to give compound P42 (2.11 g, 72%) as a white solid.
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; water; at 100.0℃; for 1.5h;Inert atmosphere; Microwave irradiation;
Step 1 : Methyl 3-(1-(cvclohexylmethyl)-5-methyl-4-(oxetan-3-ylcarbarnoyl)-1 --pyrrol-2-vn-5- (trifluoromethyl)benzoate (13) A mixture of 5-bromo-1-(cyclohexylmethyl)-2-methyl-/V-(oxetan-3-yl)-1 H-pyrrole-3- carboxamide (1.54 g, 4.66 mmol), compound P68 (1.50 g, 4.24 mmol), K2C03 (1.46 g, 10.6 mmol) and TBAB (60 mg, 0.18 mmol) in 1 ,4-dioxane/H2O(10 mLJ5 ml_) was added Ph(PPh3)2CI2 (300 mg) under N2. The solution was heated under microwave conditions at 100C for 1.5 h. Water was added and the solution was extracted with EA. The organic layer was washed with brine, dried over NaS04, filtered, concentrated and purified by CC (PE/EA = 5/1) to give compound 13 (1.12 g, 63%) as a colorless solid.
3,5-dimethoxyphenyl 2,3,4,5,6-pentafluorobenzenesulfonate[ No CAS ]
methyl 3',5’-dimethoxy-5-(trifluoromethyl)[1,1'-biphenyl]-3-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89%
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate; In tert-butyl alcohol; at 28.0℃; for 12.0h;Schlenk technique; Inert atmosphere; Sealed tube;
General procedure: Procedure A: To a Schlenk tube equipped with a magnetic stiring bar and a teflon septum was charged K3PO4.H2O (1.5 mmol, 3 equiv), aryl pentafluorobenzene sulfonate (0.5 mmol, 1.0 equiv), aryl boronic acid (0.75 mmol, 1.5 equiv) and Pd(PPh3)2Cl2 (0.015 mmol, 3 mol%). The tube was then capped with a rubber septum, evacuated and backfilled with nitrogen and this cycle was repeated twice. Under an inertatmosphere, tert - butanol (3 mL) was added via syringe. Under a positive pressure of nitrogen, the rubber septum was replaced with a Teflon screw cap and this was sealed. The Schlenk tube was stirred at room temperature for the time indicated. When the reaction was completed according to TLC or GCMS (FID), thereaction mixture was diluted with EtOAc (5 mL) and filtered through celite bed. The organic layer was concentrated under reduced pressure. The residue was purified through silica gel (230 - 400 mesh) column chromatography using 1-10% ethyl acetate in petroleum ether to afford the product.
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