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With sodium carbonate; In ethanol; at 80.0℃; for 3.0h;
Example 2a. 8-fluorophenanthridin-6-ol.A mixture of m<strong>[139911-28-7]ethyl 2-bromo-5-fluorobenzoate</strong> (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80 C for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 75 - 100℃; for 8.08333h;Inert atmosphere;
General procedure: A solution of 2 M Na2CO3 (10 mL) was added under nitrogen to a 2-bromoaniline (10 mmol) in 60 mL dioxane. After 5 min stirring at 75 C, Pd[P(C6H5)3]4 was added followed by (10 mmol) of a 2-cyanophenylboronic acid pinacol ester. The reaction was stirred 8 h at 100 C. After cooling to rt the mixture was vacuum concentrated to half of its initial volume and extracted with CH2Cl2 (30 mL) and water (30 mL). The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4 and evaporated. The solid crystallized upon concentration.
7-(2-aminophenyl)-3.4-dihydro-2H-1-benzopyran-4-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; at 60℃; for 4h;Inert atmosphere;
Into a 2-L 3-necked round- bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(3- bromophenoxy)propanoic acid (73 g, 297.87 mmol, 1.00 equiv), tetrahydrofuran (750 mL), 2- (tetramethyl-l,3,2-dioxaborolan-2-yl)aniline (57 g, 260.17 mmol, 1.30 equiv), 1M K3P04 (307 mL, 3.00 equiv), and Pd(dppf)Cl2 (25 g, 34.17 mmol, 0.10 equiv). The resulting solution was stirred for 4 h at 60C in an oil bath, then extracted with of ethyl acetate (2x500 mL). The combined organic layers were washed with of water (1x500 mL) and of brine (1x500 mL), then dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was purified on a silica gel column eluting with ethyl acetate/hexane (1 : 10) to give the title compound
With potassium phosphate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In tetrahydrofuran; at 60℃; for 4h;Inert atmosphere;
Into a 2-L 3-necked round bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-(3- bromophenoxy)propanoic acid (73 g, 297.87 mmol, 1.00 equiv), tetrahydrofuran (750 mL), 2- (tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (57 g, 260.17 mmol, 1.30 equiv), 1M K3P04 (307 mL, 3.00 equiv), and Pd(dppf)C12 (25 g, 34.17 mmol, 0.10 equiv). The resulting solution wasstirred for 4 h at 60C in an oil bath, then extracted with of ethyl acetate (2x500 mL). The combined organic layers were washed with of water (1x500 mL) and of brine (1x500 mL), then dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting residue was purified on a silica gel column eluting with ethyl acetate/hexane (1:10) to give the title compound.
9-(trifluoromethyl)phenanthridin-6-amine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73%
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In ethanol; water; toluene; for 24.0h;Reflux;
2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline is dissolved in toluene and placed in a two-neck flask.Add Tripotassium phosphate, Pd (PPh3) 2Cl2 and Ethanol dissolved in water. After 5 minutes, add 2-bromo-4- (trifluoromethyl) benzonitrile. Allow to reflux for 24 hours. When the reaction is complete, extract with CH2Cl2. Purification by silica gel column (yield: 73%)
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