Structure of 6948-30-7
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CAS No. : | 6948-30-7 |
Formula : | C9H9BrO3 |
M.W : | 245.07 |
SMILES Code : | COC1=CC(C=O)=CC(Br)=C1OC |
MDL No. : | MFCD00003346 |
InChI Key : | ICVODPFGWCUVJC-UHFFFAOYSA-N |
Pubchem ID : | 81379 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With ammonium acetate; In toluene; for 8h;Reflux; | General procedure: The substituted 1-(1H-indol-3-yl)ethanone (1 mmol), together with the respective benzaldehyde (1 mmol), malononitrile (1 mmol) and ammonium acetate (8 mmol) were dissolved in toluene (30 mL) and heated to reflux for 8 h. The solvent was removed under reduced pressure and absolute ethanol was added to the residue. The precipitate was collected by filtration and purified by silica gel column chromatography to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 80℃; for 18h; | Example 13:7-Amino-4-hydroxy-5-(3,4,5-trifluoro-phenyl)-5H-pyrano[2,3-d]pyrimidine-6-carbonitrile (13)(13)4,6-Dihydroxypyrimidine (493 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for lh and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.43 g, 3.53 mmol, 80 %). |
80% | With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 20 - 80℃; for 18h; | 4,6-Dihydroxypyrimidine (493 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for lh and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.43 g, 3.53 mmol, 80 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.8% | 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 80℃; for 18h; | Example 12:7-Amino-4-hydroxy-2-methyl-5-(3,4,5-trifluoro-phenyl)-5H-pyrano[2,3-d]pyrimidine-6- carbon (12)(12)4,6-Dihydroxy-2-methylpyrimidine (555 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol ) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.38 g, 3.29 mmol, 74.8 % of the theoretical yield). |
74.8% | With 1,4-diaza-bicyclo[2.2.2]octane; In ethanol; at 20 - 80℃; for 18h; | 4,6-Dihydroxy-2-methylpyrimidine (555 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol ) and then stirred at 80 C under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50 % aqueous ethanol and dried under vacuum (1.38 g, 3.29 mmol, 74.8 % of the theoretical yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8.5% | With piperidine; In ethanol; at 80℃; for 16h;Inert atmosphere; | General procedure: To a mixture of 9 (100mg, 0.74mmol) (the general procedure for the synthesis of intermediate 9 was presented in supporting information), 3-chlorobenzaldehyde (104mg, 0.74mmol) and ethyl 2-cyanoacetate (83μL, 0.78mmol) in anhydrous EtOH (5mL) was added piperdine (136μL, 1.48mmol). The reaction mixture was stirred for 16hat 80C under N2 atmosphere. The resulting reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography eluting with CH2Cl2/MeOH (200:1-100:1, v/v) to afford the title compound (9a) as a slight yellow solid (210mg, 77% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With piperidine; In ethanol; at 80℃; for 16h;Inert atmosphere; | General procedure: To a mixture of 9 (100mg, 0.74mmol) (the general procedure for the synthesis of intermediate 9 was presented in supporting information), 3-chlorobenzaldehyde (104mg, 0.74mmol) and ethyl 2-cyanoacetate (83muL, 0.78mmol) in anhydrous EtOH (5mL) was added piperdine (136muL, 1.48mmol). The reaction mixture was stirred for 16hat 80C under N2 atmosphere. The resulting reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography eluting with CH2Cl2/MeOH (200:1-100:1, v/v) to afford the title compound (9a) as a slight yellow solid (210mg, 77% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With piperidine; In ethanol; at 80℃; for 16h;Inert atmosphere; | General procedure: To a mixture of 9 (100mg, 0.74mmol) (the general procedure for the synthesis of intermediate 9 was presented in supporting information), 3-chlorobenzaldehyde (104mg, 0.74mmol) and ethyl 2-cyanoacetate (83μL, 0.78mmol) in anhydrous EtOH (5mL) was added piperdine (136μL, 1.48mmol). The reaction mixture was stirred for 16hat 80C under N2 atmosphere. The resulting reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography eluting with CH2Cl2/MeOH (200:1-100:1, v/v) to afford the title compound (9a) as a slight yellow solid (210mg, 77% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In ethanol; at 80℃; for 16h;Inert atmosphere; | General procedure: To a mixture of 9 (100mg, 0.74mmol) (the general procedure for the synthesis of intermediate 9 was presented in supporting information), 3-chlorobenzaldehyde (104mg, 0.74mmol) and ethyl 2-cyanoacetate (83muL, 0.78mmol) in anhydrous EtOH (5mL) was added piperdine (136muL, 1.48mmol). The reaction mixture was stirred for 16hat 80C under N2 atmosphere. The resulting reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography eluting with CH2Cl2/MeOH (200:1-100:1, v/v) to afford the title compound (9a) as a slight yellow solid (210mg, 77% yield). |
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