Alternatived Products of [ 553663-65-3 ]
Product Details of [ 553663-65-3 ]
CAS No. : | 553663-65-3 |
MDL No. : | MFCD28155007 |
Formula : |
C12H7Br2N
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | SAGKZGMCGWAMEE-UHFFFAOYSA-N |
M.W : |
325.00
|
Pubchem ID : | 12045830 |
Synonyms : |
|
Safety of [ 553663-65-3 ]
Signal Word: | Warning |
Class: | N/A |
Precautionary Statements: | P305+P351+P338 |
UN#: | N/A |
Hazard Statements: | H315-H319 |
Packing Group: | N/A |
GHS Pictogram: |
|
Application In Synthesis of [ 553663-65-3 ]
* 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.
- Upstream synthesis route of [ 553663-65-3 ]
- Downstream synthetic route of [ 553663-65-3 ]
- 1
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[ 544-92-3 ]
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[ 553663-65-3 ]
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[ 553663-66-4 ]
- 2
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[ 1049017-32-4 ]
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[ 553663-65-3 ]
- 3
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[ 3244-54-0 ]
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[ 553663-65-3 ]
- 4
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[ 104294-50-0 ]
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[ 553663-65-3 ]
- 5
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[ 553663-65-3 ]
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1,8-bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)-9H-carbazole
[ No CAS ]
- 6
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[ 17997-47-6 ]
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[ 553663-65-3 ]
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[ 1049017-37-9 ]
- 7
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[ 1066-54-2 ]
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[ 553663-65-3 ]
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1,8-bis[(trimethylsilyl)ethynyl]-9H-carbazole
[ No CAS ]
- 8
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[ 553663-65-3 ]
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1,1',8,8',9,9'-bicarbazole
[ No CAS ]
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[3]cyclo-1,8-carbazolylene
[ No CAS ]
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[4]cyclo-1,8-carbazolylene
[ No CAS ]
- 9
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[ 292638-84-7 ]
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[ 553663-65-3 ]
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1,8-bis((E)-styryl)-9H-carbazole
[ No CAS ]
- 10
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[ 553663-65-3 ]
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1,8-diformyl-9H-carbazole
[ No CAS ]
- 11
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[ 553663-65-3 ]
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C32H26N6
[ No CAS ]
- 12
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[ 625385-37-7 ]
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[ 553663-65-3 ]
- 13
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pyridin-2-ylzinc(II) bromide
[ No CAS ]
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[ 553663-65-3 ]
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C17H11BrN2
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
73% |
|
11.7 grams (g) (36 millimoles, mmol) of Intermediate lAand 1.45 g (35 mmol) of 60% sodium hydride were dissolved in 400 mL of tetrahydroffiran (THF), stirred at a temperature of -78C. for about 10 minutes, and then stirred at room temperature for about 2 hours. Then, 20 mL (1.76 mmol) of tetrakis(triphenylphosphine)palladium (0) and 79 mL (39.5 mmol) of 0.5 M (molar) 2-pyridylzinc bromide dissolved in THF were added thereto and heated under reflux at a temperature of 80 C. for about 16 hours. When the reaction was completed, the mixture was cooled to room temperature, added to a saturated sodium hydrogen carbonate aqueous solution, and an organic layer was extracted therefrom by using dichloromethane. The extracted organic layer was dried by using magnesium sulfate and distilled under reduced pressure. The residue obtained therefrom was separated and purified by silica gel column chromatography to obtain 8.5 g (73%) of Intermediate 1-3. The obtained compound was identified by LC-MS.j0295] LC-MS mlz=323.01 (M+H). |
73% |
|
[0278] 11.7 grams (g) (36 millimoles, mmol) of IntermediatelA and 1.45 g (35 mmol) of 60% sodium hydride weredissolved in 400 milliliters (mL) of tetrahydrofuran (THF),stirred at a temperature of -78 C. for about 10 minutes, andthen stirred at room temperature for about 2 hours. 20 mL(1.76 mmol) of tetrakis(triphenylphosphine)palladium(O)and 79 mL (39.5 mmol) of 0.5 molar (M) 2-pyridylzincbromide, which were dissolved in THF, were added thereto.The resultant mixture was heated under reflux at a temperatureof 80 C. for about 16 hours. After the reaction wascomplete, the resultant mixture was cooled to room temperature,and a saturated sodium hydrogen carbonate aqueoussolution was added thereto. The organic layer extractedwith dichloromethane was dried over magnesium sulfate,and the solvent was distilled off under reduced pressure. Thecompound obtained therefrom was separated and purified bycolunm chromatography to obtain 8.5 g (73%) of Intermediate1-4. The obtained compound was identified by LC-MS.[0279] LC-MS m/z=323.01 (M+Ht. |
- 14
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[ 553663-65-3 ]
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C28H19N3
[ No CAS ]
- 15
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[ 553663-65-3 ]
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C23H23BN2O2
[ No CAS ]
- 16
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[ 553663-65-3 ]
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C28H19N3
[ No CAS ]
- 17
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[ 553663-65-3 ]
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C28H17N3Pt
[ No CAS ]
- 18
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[ 553663-65-3 ]
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C28H17N3Pt
[ No CAS ]
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[ 553663-65-3 ]
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C28H17N3Pt
[ No CAS ]
- 20
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[ 553663-65-3 ]
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C28H15N3Pt
[ No CAS ]
- 21
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[ 553663-65-3 ]
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C36H22N10Pt2
[ No CAS ]
- 22
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[ 553663-65-3 ]
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C18H12ClN5Pt
[ No CAS ]
- 23
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[ 288-32-4 ]
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[ 553663-65-3 ]
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1,8-bis(imidazole)carbazole
[ No CAS ]
- 24
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[ 3842-55-5 ]
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[ 553663-65-3 ]
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[ 2451125-32-7 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 15 h / 60 °C
2.1: potassium phosphate; copper(l) iodide / 1,4-dioxane / 0.17 h / 20 °C
2.2: 24 h / 130 °C |
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- 25
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[ 3842-55-5 ]
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[ 553663-65-3 ]
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C27H16Br2N4
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
80% |
Stage #1: 1,8-dibromo-9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 60℃; for 15h; |
2 Preparation of Intermediate 2-a
1,8-dibromo-9H-carbazole 30 g (92.3 mmol), sodium hydride (60%) 7.4 g (184.6 mmol) were suspended in 650 ml of dimethylformamide and stirred at room temperature for 10 minutes. Then, 29.6 g (110.8 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was suspended in 200 ml of dimethylformamide and added, followed by stirring at 60° C. for 15 hours. After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and then subjected to silica gel column to obtain Intermediate 2-a, 41.1 g (yield: 80%). |
80% |
Stage #1: 1,8-dibromo-9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: 2-chloro-4,6-diphenyl-1,3,5-triazine In N,N-dimethyl-formamide at 60℃; for 15h; |
3 Preparation of Intermediate 3-a
1,8-dibromo-9H-carbazole 30 g (92.3 mmol), sodium hydride (60%) 7.4 g (184.6 mmol) was suspended in 650 ml of dimethylformamide and stirred at room temperature for 10 minutes.Then, 29.6 g (110.8 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was suspended in 200 ml of dimethylformamide and added, followed by stirring at 60° C. for 15 hours.After the reaction was completed, the mixture was extracted with dichloromethane and distilled water, and the organic layer was distilled under reduced pressure and then subjected to silica gel column to obtain intermediate 3-a, 41.1 g (yield: 80%). |
- 26
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[ 3842-55-5 ]
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[ 553663-65-3 ]
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[ 2448492-23-5 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 20 °C
1.2: 15 h / 60 °C
2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 12 h / Reflux |
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- 27
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[ 553663-65-3 ]
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[ 2531444-70-7 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: potassium hydroxide; 1,10-Phenanthroline; copper(l) iodide / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / Inert atmosphere; Reflux
2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 12 h / 80 °C |
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- 28
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[ 553663-65-3 ]
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[ 2531409-53-5 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps
1: potassium hydroxide; 1,10-Phenanthroline; copper(l) iodide / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / Inert atmosphere; Reflux
2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 12 h / 80 °C
3: sodium t-butanolate; bis(tri-t-butylphosphine)palladium(0) / toluene / 12 h / 110 °C |
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- 29
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[ 553663-65-3 ]
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[ 2531409-89-7 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 3 steps
1: potassium hydroxide; 1,10-Phenanthroline; copper(l) iodide / 5,5-dimethyl-1,3-cyclohexadiene / 8 h / Inert atmosphere; Reflux
2: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 12 h / 80 °C
3: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 12 h / 80 °C |
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- 30
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[ 591-50-4 ]
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[ 553663-65-3 ]
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[ 2368260-02-8 ]
Yield | Reaction Conditions | Operation in experiment |
64% |
With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene for 8h; Inert atmosphere; Reflux; |
Synthesis of Intermediate 1-1
The compound under nitrogen atmosphere 1,8-dibromo-9H-carbazole (20.0g, 61.94mmol)And iodobenzene (12.6g, 61.94mmol) are completely dissolved in xylene 70ml, and potassium hydroxide (5.6g, 99.10mmol) and 1,10-phenanthroline (11.2g, 61.94mmol) was added and stirred while raising the temperature until refluxed. When it starts to reflux copper iodide (14.2g, 74.33mmol) was divided into a solid state several times. After 8 hours, the reaction was terminated and the temperature was lowered to room temperature.After filtering silica, concentrated under reduced pressureColumn purification to intermediate 1-1 (15.8g, 64% yield)Was prepared. |
- 31
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[ 553663-65-3 ]
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[ 679836-62-5 ]
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[ 2647390-07-4 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With potassium carbonate In dimethyl sulfoxide at 120℃; for 8h; Inert atmosphere; |
1 Synthesis of Intermediate 3
Under a nitrogen atmosphere, add 1mmol Intermediate 1 and 2.1mmol Intermediate 2 into a dry three-necked flask, pour 100ml of DMSO as a solvent, add dry K2CO3 as a base, and react at 120 for 8 hours. TLC monitoring After the reaction is complete, the reaction solution is cooled to room temperature, water and dichloromethane are added in sequence, the reaction solution is washed with water several times, and the aqueous phase is extracted with dichloromethane several times. The organic phases are combined and dried with anhydrous Na2CO3. Filter and spin dry the reaction solution to obtain a crude product, which is recrystallized with ethyl acetate to obtain a molar weight of Intermediate 3 of 0.78 mmol. The reaction yield is 78%. |
- 32
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[ 86-74-8 ]
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[ 553663-65-3 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; bis(trifluoromethyl sulfate)palladium / toluene / 12 h / 180 °C
2: N-Bromosuccinimide; Iron(III) trifluoromethanesulfonate / benzene / 6 h / 90 °C |
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- 33
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[ 16807-11-7 ]
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[ 553663-65-3 ]
Yield | Reaction Conditions | Operation in experiment |
75% |
With N-Bromosuccinimide; Iron(III) trifluoromethanesulfonate In benzene at 90℃; for 6h; |
17 Example 17: Preparation of 1,8-dibromocarbazole (17) from 1-bromocarbazole.
Under air atmosphere, add iron methanesulfonate (2mol%, 1.5mg), 1-bromocarbazole (0.2mmol, 48.9mg), NBS (0.22mmol, 39.2mg) and magnetic stirrer to 35mL glass withstand pressure In the tube. Then benzene (10 mL) was added, and the reaction tube was reacted at 90°C for 6 hours. After the reaction is complete, cool the reaction system to room temperature, open the reaction vessel at room temperature, add 10 mL of water; extract with 30 mL of dichloromethane, collect the organic phase, dry the organic phase with anhydrous sodium sulfate, and purify the organic layer by column chromatography. The yield of the pure product is 75%, and the gas phase selectivity of the ortho position and the para position is o:p=92:8. |