Structure of 914306-89-1
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CAS No. : | 914306-89-1 |
Formula : | C34H20Br2 |
M.W : | 588.33 |
SMILES Code : | BrC1=CC2=C(C3=C4C=CC=CC4=CC=C3)C5=CC=C(Br)C=C5C(C6=C7C=CC=CC7=CC=C6)=C2C=C1 |
MDL No. : | MFCD16660915 |
InChI Key : | HDGCGHBEIGZDSX-UHFFFAOYSA-N |
Pubchem ID : | 58855126 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H413 |
Precautionary Statements: | P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
* 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 |
---|---|---|
With Ki; NaH2PO2; In diethyl ether; water; acetic acid; | (1) Synthesis of 2,6-dibromo-9,10-di-1-naphthylanthracene 5 g of 1-naphthyl lithium was dissolved in Et2O, and the resulting solution was gradually added dropwise to a solution containing 5 g of 2,6-dibromoanthraquinone dissolved in Et2O. This reaction was carried out on a dry ice bath. Then, the temperature of the reaction material was elevated to room temperature, thereby obtaining an intermediate product. The obtained intermediate product was filtered, thereby obtaining white solids. The white solids thus obtained were dissolved in 100 mL of AcOH, followed by addition of KI and NaH2PO2 and the mixture was stirred at 130C for 24 hours. When the reaction was complete, the reaction material was filtered with addition of water. The filtrate was recrystallized from MC and MeOH, thereby obtaining 4 g of 2,6-dibromo-9,10-di-1-naphthylanthracene. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.1% | a) 2,6-Dibromo-9,10-bis(naphth-1-yl)anthracene The corresponding Grignard reagent is prepared from 30.5 ml (220 mmol) of 1-bromonaphthalene and 5.5 g (225 mmol) of magnesium in 500 ml of THF. 36.6 g (100 mmol) of 2,6-dibromoanthraquinone are added to this Grignard reagent, the mixture is refluxed for 6 h and allowed to cool, 15 ml of acetic acid are added, the mixture is evaporated to dryness, the residue is taken up in 500 ml of DMF, 56.9 g (300 mmol) of tin(II) chloride are added, and the mixture is refluxed for 5 h. After cooling, 200 ml of 2N hydrochloric acid are added, the mixture is stirred for a further 1 h, the solid is filtered off with suction, washed three times with 200 ml of 2N hydrochloric acid each time, three times with 300 ml of water each time, and three times with 200 ml of ethanol each time, dried under reduced pressure and recrystallised once from DMF. Yield: 48.9 g (83 mmol), 83.1% of theory; purity: 98% according to 1H-NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: a 3-bromopyridine 5.45 g (34.5 mmol) to THF 60 mL nBuLi 13.8 mL (34.5 mmol, 2.5M in hexane) was dissolved in -78Then slowly added dropwise in , stirred for 1 hour. 2-bromo -4a to the reaction solution, 9a- dihydro-anthraquinoneIt was added dropwise 4.33 g (15.0 mmol) slowly and stirred at room temperature for 12 hours. Inflicting a 60 mL of water to the reaction solutionAnd extracted three times with ethyl acetate and then 50 mL were The combined organic layers were dried over magnesium sulfate. After evaporation of the solventsTo the resulting residue was 22.4 g KI (135 mmol) was dissolved with Na2H2PO2 · H2O 21.3 g (165 mmol) in 50 mL acetic acid 120 was stirred for 1 hour. After cooling the reaction solution to room temperature, water was added to the obtained residue was filtered 60 mL water chamberRica jelgwan separated by chromatography to give the intermediate I-11 5.05 g (82% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h; | Intermediate I-12 6.18 g (10.5 mmol), 2 - pyridyl boronic acid 1.29 g (10.5 mmol), Pd (PPh3) 4 0.61 g (0.53 mmol) and Dissolve 4.35 g K2CO3 (31.5 mmol) in 60 mL THF and 30 mL H2O was stirred at 80 for 12 hours. After cooling the reaction solution to room temperature and extracted three times with 30 mL water and 30 mL ethyl acetate. The combined organic layers were dried over magnesium sulfate, and the compound of the residue obtained by evaporation of the solvent, separated by silica chromatography purification jelgwan I-13 4.19 g (Yield: 68%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 80℃; for 1h;Inert atmosphere; | 2 opening having composite multi function cap 250 ml (10) (0.6g, 1.02mmol), delta-carboline (0.38g, 2.24mmol), NaO t Bu (0.29g, 3.06mmol) for toluene (100 ml) under nitrogen paste has better mouth feeling and which agitates the, reaction temperature by 1 80 C reacted time at elevated temperatures. Herein Pd (dba) 2 (0.02g, 0.03mmol), (tert-Bu) 3 P (0.01g, 0.04mmol) adding an 1-2 reacted in 80 C days. Said reaction solution to filter out remove the salt. Filtrate distilled to remove the toluene column citrus the compounds separated 0.35g (3-18, DdC3-1N-AnT) (yield: 45%)is obtained. |
45% | 2-necked 250ml flask, the compound (10) (0.6g, 1.02mmol), delta-carboline (0.38g, 2.24mmol), NaOtBu (0.29g, 3.06mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 and reacted for 1 hour. To the resulting solution was added Pd (dba) 2 (0.02g, 0.03mmol), (tert-Bu) 3P (0.01g, 0.04mmol) and the reaction was performed at 80 for 1-2 days. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain the compound (3-18, 1N-AnT-DdC3) 0.35g: (yield: 45%). | |
45% | 2-necked 250ml flask, the compound (10) (0.6g, 1.02mmol), delta-carboline (0.38g, 2.24mmol), NaOtBu (0.29g, 3.06mmol) were placed in toluene (100ml) was stirred under nitrogen, and the reaction temperature the temperature was raised to 80 C and reacted for 1 hour. To the resulting solution was added Pd(dba)2 (0.02g, 0.03mmol), (tert-Bu)3P (0.01g, 0.04mmol) and the reaction was performed at 80 C for 1-2 days. Filtering the reaction solution to remove salts. Remove the toluene was evaporated from the solution by filtration, remove the concentrate to the column to obtain the compound (3-18, 1N-AnT-DdC3) 0.35g: (yield: 45%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With NaH2PO2; acetic acid; potassium iodide; at 80 - 90℃; for 2h;Reflux; Inert atmosphere; | 2-necked 500ml flask was charged with compound (9) (4.7g, 0.01mol), KI (4.5g, 0.04mol) NaH2PO2 (4.5g, 0.07mol), 2 hr reflux insert as the AcOH (200ml) at 80 ~ 90oC under a nitrogen It was. Lower the temperature of the solid was washed with water and then filtered. Dissolve the solid in MC was extracted with distilled water and Methylene Chloride. After the extraction of the water japahjun Methylene Chloride layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a yellow solid. This solid was recrystallized as Toluene to give a yellow solid (10). (3.5g, 78%) |
78% | With sodium hypophosphite; acetic acid; potassium iodide; at 80 - 90℃; for 2h;Inert atmosphere; | 2-necked 500ml flask was charged with compound (9) (4.7g, 0.01mol), KI (4.5g, 0.04mol) NaH2PO2 (4.5g, 0.07mol), 2 hr reflux insert as the AcOH (200ml) at 80~90C under a nitrogen It was. Lower the temperature of the solid was washed with water and then filtered. Dissolve the solid in MC was extracted with distilled water and Methylene Chloride. After the extraction of the water japahjun Methylene Chloride layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a yellow solid. This solid was recrystallized as Toluene to give a yellow solid (10). (3.5g, 78%) |
45% | With sodium hypophosphite; acetic acid; potassium iodide; at 80 - 90℃; for 2h;Inert atmosphere; | 2 opening having composite multi function cap 500 ml (9) (4.7g, 0.01mol), KI (4.5g, 0.04mol) NaH 2 PO 2 (4.5g, 0.07mol), AcOH (200 ml) together in a under nitrogen into the 80-90 o C in the reflux time 2. After filtering solid after my phosphorus temperature is washing water. Solid is dibutyl phthalate or dimethyl MC Methylene Chloride and a distilled water by extracting with him. Extracted Methylene Chloride layer MgSO 4 after for holding a order to form an exterior, of methanol removing the solvent by the yellow solid obtained. The solid a solid yellow in recrystallization Toluene (10) a obtained. (3.5g, 78%) |