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Chemical Structure| 6948-30-7 Chemical Structure| 6948-30-7

Structure of 6948-30-7

Chemical Structure| 6948-30-7

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Product Details of [ 6948-30-7 ]

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

Safety of [ 6948-30-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 6948-30-7 ]

* 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.

  • Downstream synthetic route of [ 6948-30-7 ]

[ 6948-30-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 19012-02-3 ]
  • [ 6948-30-7 ]
  • [ 109-77-3 ]
  • 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-6-(1-methyl-1H-indol-3-yl)nicotinonitrile [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 6948-30-7 ]
  • [ 1193-24-4 ]
  • [ 109-77-3 ]
  • [ 951922-50-2 ]
YieldReaction ConditionsOperation 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 %).
  • 3
  • [ 6948-30-7 ]
  • [ 1194-22-5 ]
  • [ 109-77-3 ]
  • [ 1375352-57-0 ]
YieldReaction ConditionsOperation 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).
  • 4
  • [ 6948-30-7 ]
  • [ 85926-99-4 ]
  • [ 105-56-6 ]
  • ethyl 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-4,7,8,9-tetrahydropyrano[2,3-e]indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 5
  • [ 58196-33-1 ]
  • [ 6948-30-7 ]
  • [ 105-56-6 ]
  • ethyl 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-6,7,8,9-tetrahydro-4H-pyrano[3,2-g]quinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 6
  • [ 6948-30-7 ]
  • [ 85926-99-4 ]
  • [ 109-77-3 ]
  • 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-4,7,8,9-tetrahydropyrano[2,3-e]indole-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation 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).
  • 7
  • [ 58196-33-1 ]
  • [ 6948-30-7 ]
  • [ 109-77-3 ]
  • 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-6,7,8,9-tetrahydro-4H-pyrano[3,2-g]quinoline-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation 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).
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reactions of Ethers • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 6948-30-7 ]

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Aldehydes

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Ethers

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