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With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 3.0h;Heating / reflux;
A solution of <strong>[73220-41-4]3-bromo-7-methoxy-chromen-4-one</strong> (2.5 g, 10 mmol), 2,5-dimethoxyphenylboronoic acid (2.73 g, 15 mmol), 2M Na2CO3 (30 ml), and Pd(PPh3)4 (0.30 g, 0.3 mmol) in toluene (40 ml) and EtOH (5 ml) was heated to reflux. After 3 h the reaction was cooled, and the organic layer was separated, dried, and concentrated to give an oily solid, which was triturated with MeOH and filtered to give 21 as a white solid (1.5 g, 51%).
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; for 6.0h;Heating / reflux;
A solution of <strong>[73220-41-4]3-bromo-7-methoxy-chromen-4-one</strong> (1.8 g, 7.1 mmol), 2,5-dimethoxy-3-trimethylstannyl-benzonitrile (2.3 g, 7.1 mmol), Pd(PPh3)4 (0.5 g), and CuI (0.1 g) in 50 mL dioxane was heated to reflux. After 6 h the reaction was cooled and concentrated and the product was purified by column chromatography on silica gel (EtOAc/hex; 1:4) to give 22 as a solid (0.9 g, 38%).
With sodium carbonate; In ethanol; ethyl acetate; toluene;
3-(2,4-Dimethoxy-phenyl)-7-methoxy-chromen-4-one 14 A solution of 13 (4.0 g, 15.8 mmol) and 2,4-dimethoxy benzeneboronic acid (3.4 g, 19.0 mmol) and Pd(Ph3)4 (0.79 g) in toluene/EtOH (50 mL5 mL) and 2M Na2CO3 aq. (30 mL) was heated to reflux. After 5 h, the reaction was cooled and the organic layer dried over MgSO4, concentrated and chromatographed on silica gel (EtOAc/hexanes 3:7 to EtOAc/hexanes 1:1) to yield 14 as a solid which was triturated with MeOH to give a tan solid.
3-Bromo-7-methoxy-chromen-4-one 13 Compound 12 (4.0 g, 18.1 mmol) in CH2Cl2 (50 mL) was treated with dropwise addition of Br2 (2.9 g, 18.1 mmol). After stirring for 10 min at rt, the CH2Cl2 was washed with a 10% Na2SO3 aq., dried over MgSO4 and concentrated to give a yellow solid which was triturated to yield compound 13 (2.7 g) as a white solid.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 48.0h;Reflux;
General procedure: 3-Bromo-4H-chromen-4-ones 1a,b and 1,3-dicarbonyl compounds 2b-h were prepared by following previously reported methods. 3-Bromochromone 1a,b (1.0 mmol) and 1,3-dicarbonyl compound 2a-h (1.1 mmol) were dissolved in THF (40 mL). DBU (1 drop per 50 mg of starting material) was then added and the resulting reaction mixture was stirred vigorously and heated to reflux. After 48 h, the solvent was evaporated under reduced pressure and the residue was purified by short plug silica gel column chromatography using dichloromethane as eluent. The purified products 3a-i were recrystallized from hexane/dichloromethane (1:1) by slow evaporationat 6 C.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 48.0h;Reflux;
General procedure: 3-Bromo-4H-chromen-4-ones 1a,b and 1,3-dicarbonyl compounds 2b-h were prepared by following previously reported methods. 3-Bromochromone 1a,b (1.0 mmol) and 1,3-dicarbonyl compound 2a-h (1.1 mmol) were dissolved in THF (40 mL). DBU (1 drop per 50 mg of starting material) was then added and the resulting reaction mixture was stirred vigorously and heated to reflux. After 48 h, the solvent was evaporated under reduced pressure and the residue was purified by short plug silica gel column chromatography using dichloromethane as eluent. The purified products 3a-i were recrystallized from hexane/dichloromethane (1:1) by slow evaporationat 6 C.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 48.0h;Reflux;
General procedure: 3-Bromo-4H-chromen-4-ones 1a,b and 1,3-dicarbonyl compounds 2b-h were prepared by following previously reported methods. 3-Bromochromone 1a,b (1.0 mmol) and 1,3-dicarbonyl compound 2a-h (1.1 mmol) were dissolved in THF (40 mL). DBU (1 drop per 50 mg of starting material) was then added and the resulting reaction mixture was stirred vigorously and heated to reflux. After 48 h, the solvent was evaporated under reduced pressure and the residue was purified by short plug silica gel column chromatography using dichloromethane as eluent. The purified products 3a-i were recrystallized from hexane/dichloromethane (1:1) by slow evaporationat 6 C.
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 48.0h;Reflux;
General procedure: 3-Bromo-4H-chromen-4-ones 1a,b and 1,3-dicarbonyl compounds 2b-h were prepared by following previously reported methods. 3-Bromochromone 1a,b (1.0 mmol) and 1,3-dicarbonyl compound 2a-h (1.1 mmol) were dissolved in THF (40 mL). DBU (1 drop per 50 mg of starting material) was then added and the resulting reaction mixture was stirred vigorously and heated to reflux. After 48 h, the solvent was evaporated under reduced pressure and the residue was purified by short plug silica gel column chromatography using dichloromethane as eluent. The purified products 3a-i were recrystallized from hexane/dichloromethane (1:1) by slow evaporationat 6 C.
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