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CAS No. : | 2693-46-1 | MDL No. : | MFCD00001185 |
Formula : | C16H11N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VHGJAFIHUSTRGB-UHFFFAOYSA-N |
M.W : | 217.27 | Pubchem ID : | 17599 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 hydrogenchloride at 230℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium amalgam; ethanol; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With hydrazine hydrate In ethanol for 2h; Heating; | |
With hydrogenchloride; acetic acid; tin(ll) chloride | ||
With ethanol; platinum Hydrogenation; |
(reduction); | ||
With calcium chloride; zinc In ethanol | ||
With Salmonella typhimurium TA98 In various solvent(s) at 37℃; | ||
With hydrogen In methanol at 20℃; for 1h; chemoselective reaction; | ||
With palladium 10% on activated carbon; hydrogen In ethanol for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With potassium carbonate In tetrahydrofuran; water at 20℃; for 12h; | |
With pyridine; benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
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With iodine at 200 - 220℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With acetic acid for 2.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethyl acetate at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
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65 mg | With formic acid for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
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In dichloromethane at 4℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2SO4 2: aq. H2SO4 / 280 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: H2SO4 2: aq. H2SO4 / 280 °C 3: OH- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 98 percent / AcOH / 2.5 h 2: 86 percent / ZnBr2, HMDS / benzene / 1.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 20 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / 3 h / Ambient temperature 2: 96 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating | ||
Multi-step reaction with 2 steps 1: aqueous HNO3; glacial acetic acid 2: tin (II)-chloride; acetic acid; aqueous hydrochloric acid | ||
Multi-step reaction with 2 steps 1: aqueous HNO3; glacial acetic acid 2: platinum; ethanol / Hydrogenation |
Multi-step reaction with 2 steps 1: HNO3, H2SO4 / acetic acid 2: aq. CaCl2, Zn / ethanol | ||
Multi-step reaction with 2 steps 1: nitric acid / dichloromethane; water / 2 h 2: hydrogen; palladium 10% on activated carbon / ethanol / 20 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aqueous ethanol; sodium-amalgam; acetic acid 3: sodium dichromate; water; acetic acid / und Erwaermen des Reaktionsprodukts mit aethanol. Alkalilauge |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous HCl / 230 °C 2: diluted aqueous alkaline solution; sodium-amalgam |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous ethanol; sodium-amalgam; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: I2 / 200 - 220 °C 2: AsCl3 / 1,2-dichloro-benzene / 0.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) aq. HCl, (ii) aq. NaNO2, (iii) CuCl, aq. HCl 2: Na2Cr2O7, H2SO4 / acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | 3-Aminofluoranthene, 10.85 g, 49.94 [MMOL,] is suspended in water, 50 ml, and HCI, 12 M, 10 [ML,] 0.12 mol, at [0C.] Sodium nitrite, 3.50 g, 50.7 [MMOL,] in water, 10 mi, is added dropwise over 15 minutes. After 30 minutes at [0C,] the red-brown solution is filtered. Tobias acid (2- [NAPHTHYLAMINE-1-SULFONIC] acid), 11.15 g, 49.96 [MMOL,] is dissolved in pyridine, 50 ml, and cooled to [0C.] The diazonium salt solution is then added dropwise over 30 minutes at [0C.] After 2 hours, the suspension is filtered, washed with water and dried in vacuo to give a purple-red solid. The material, 15.6 g, 42.0 [MMOL,] is heated in pyridine, 250 ml, to [60C] in a 1 I reactor. Copper [(IL)] sulfate pentahydrate, 26.4 g, 0.105 mol, in water, 100 mi, is added dropwise to the azo compound. The temperature is then raised to [90C] for 4 hours. The mixture is cooled to room temperature and filtered to give a pale brown solid. The compound is purified by crystallization. Yield, 7.9 g, 21.4 mmol, [51%. TM = 155C.] MS [(APCI)] : 370.1 (M+1). The material has a [XMAE] eMAHsion of 478 nm in solution. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With acetic acid In ethanol at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.1% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere; Darkness; | 1.1 (Example 1) Synthesis of Exemplified Compounds D1 and D2; Exemplified Compounds D1 and D2 were synthesized according to a synthesis method to be described below.; (1) Synthesis of Intermediate Compound M1; Under an argon atmosphere, the following reagent and solvent were loaded into a 2-L four-necked flask. 3-Aminofluoranthene:45.4 g (209 mmol) DMF:910 mL Next, the reaction solution was cooled to 0°C with an ice bath in a state where the inside of the reaction system was shielded from light. Next, NBS (37.2 g, 209 mmol) was added to the reaction solution. After that, the ice bath was removed, and then the temperature of the reaction solution was returned to room temperature. Next, the reaction solution was stirred at room temperature for 1 hour. Next, a crystal (yellowish green crystal) precipitated at the time of the injection of the reaction solution into 2 L of ice water was taken by filtration. Next, the crystal taken by filtration was dissolved in 4 L of ethyl acetate, and then the solution was sequentially passed through 50 g of magnesium sulfate and 500 g of Florisil so that the raw material substance was removed. Next, a slurry-like substance produced at the time of the concentration of the filtrate under reduced pressure was filtered. Thus, a crystal was obtained. Next, the resultant crystal was dried under reduced pressure. Thus, 54.0 g of 2-bromofluoranthene-3-amine were obtained (yield: 87.1%). |
83% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h; | 1 Synthesis of Exemplary Compound A12; 5.08 g (29 mmol) of N-bromosuccinimide (NBS) was added to 5.9 g (27 mmol) of Y1 in 250 ml of N,N-dimethylformamide at room temperature. After agitation for four hours, 100 ml of toluene and 250 ml of water were added to the solution, which was then extracted with toluene. The extract was washed twice with 100 ml each of water. After the organic phase was dried over magnesium sulfate, the solution was filtered. The filtrate was concentrated and recrystallized in toluene, yielding 6.6 g (yield = 83%) of a brown solid Y2. |
60% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; | 1 [0099] First, 10.5 g (48 mmol) of fluoranthene-3-amine (El) was mixed in 300 mL of dimethylformamide at 00C, and 8.2 g (48 mmol) of N-bromosuccinimide was added to the mixture. The temperature of the reaction mixture was returned to the room temperature, and the mixture was stirred for eight hours. The mixture was poured into water, and the precipitate was filtered and then recrystallized with ethanol . After the crystals were filtered, the crystals were washed with heptane, and then dried. As a result, 29 g of a brown solid E2 was obtained (yield: 60%) . |
60% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; | 1 EXAMPLE 1 In 300 ml of dimethylformamide, 10.5 g (48 mmol) of fluoranthene-3-amine (E1) was mixed at 0°C, 8.2 g (48 mmol) of N-bromosuccimide was added thereto, and the resulting mixture was returned to room temperature and stirred for 8 hours. The mixture was discharged into water, precipitates were filtered, and recrystallization was conducted in ethanol. Crystals are filtered, washed with heptane, and dried. As a result, 29 g (yield: 60%) of dark brown solid E2 was obtained. |
60% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; | 1 0088] First, 10.5 g (48 mmol) of fluoranthene-3-amine (E1) was mixed with 300 mL of dimethylformamide at 0 degrees (Celsius). Next, 8.2 g (48 mmol) of N-bromosuccinimide was added to the mixture. The temperature was returned to room temperature, and the reaction mixture was stirred for eight hours. The reaction mixture was poured into water, and a precipitate was filtered. The precipitate was then recrystallized with ethanol. The resulting crystals were filtered, washed with heptane, and then dried. Thus, 29 g of a brown solid E2 was obtained (yield: 60%). Subsequently, 10 g (34 mmol) of E2 was put in a 500-mL round-bottom flask, and the inside of the reaction system was replaced with argon. Next, 150 mL of methoxycyclopentane was put in the flask in an argon atmosphere, and the solution was cooled to -75 degrees (Celsius). Next, 64 mL of a 1.6 M solution of n-butyllithium was added dropwise thereto. After the dropwise addition, the temperature of the reaction mixture was returned to room temperature, and stirring was conducted for one hour. Subsequently, the reaction mixture was again cooled to -75 degrees (Celsius), and 15 g of finely crushed dry ice was added to the mixture. The temperature of the reaction mixture was gradually returned to room temperature. After the temperature was returned to room temperature, stirring was conducted for eight hours, and 1 M hydrochloric acid was then added to the reaction mixture to terminate the reaction. Subsequently, extraction was conducted with ethyl acetate. The organic layer was concentrated to obtain a brown liquid. The liquid was purified by column chromatography (ethyl acetate/heptane = 1:3), and recrystallized with chloroform/methanol. Thus, 2.5 g of E3 was obtained in the form of a brown powder (yield: 28%). |
60% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 8h; | 1 Example 1; [Synthesis of A110 and A110-2]; [0130] An isomer of example compound A110 is expressed as "A110-2" .[0131][Chem. 25][0132] First, 10.5 g (48 mmol) of fluoranthene-3-amine (El) was added to 300 ml of dimethylformamide at 0°C. Next, 8.2 g (48 mmol) of N-bromosuccinimide was added to the mixture. The temperature was returned to room temperature, and the mixture was stirred for eight hours. The resultant precipitate was filtered in water and then recrystallized with ethanol. The crystal was filtered, washed with heptane, and then dried. Thus, 29 g of brown solid E2 was obtained (yield: 60%) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C 4.1: potassium <i>tert</i>-butylate / diethyl ether; tetrahydrofuran / 1 h / 20 °C 4.2: 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C 4.1: potassium <i>tert</i>-butylate / diethyl ether; tetrahydrofuran / 1 h / 20 °C 4.2: 5 h / 20 °C 5.1: methanesulfonic acid / dichloromethane / 17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C 4.1: potassium <i>tert</i>-butylate / diethyl ether; tetrahydrofuran / 1 h / 20 °C 4.2: 5 h / 20 °C 5.1: methanesulfonic acid / dichloromethane / 17 h / 20 °C 6.1: bromine / dichloromethane; chloroform / 18.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C 4.1: potassium <i>tert</i>-butylate / diethyl ether; tetrahydrofuran / 1 h / 20 °C 4.2: 5 h / 20 °C 5.1: methanesulfonic acid / dichloromethane / 17 h / 20 °C 6.1: bromine / dichloromethane; chloroform / 18.5 h / 0 - 20 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 6 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C 4.1: potassium <i>tert</i>-butylate / diethyl ether; tetrahydrofuran / 1 h / 20 °C 4.2: 5 h / 20 °C 5.1: methanesulfonic acid / dichloromethane / 17 h / 20 °C 6.1: bromine / dichloromethane; chloroform / 18.5 h / 0 - 20 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 6 h / 90 °C 8.1: potassium acetate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 3 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux 3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 4 h / 90 °C 4.1: potassium <i>tert</i>-butylate / diethyl ether; tetrahydrofuran / 1 h / 20 °C 4.2: 5 h / 20 °C 5.1: methanesulfonic acid / dichloromethane / 17 h / 20 °C 6.1: bromine / dichloromethane; chloroform / 18.5 h / 0 - 20 °C 7.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 6 h / 90 °C 8.1: potassium acetate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 3 h / 95 °C 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 3 h / 170 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 4 h / 20 °C 2.1: sulfuric acid / ethanol / 0.5 h / 0 °C 2.2: 1 h / 0 °C 2.3: 5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 - 20 °C 2.1: n-butyllithium / cyclopentyl methyl ether / -75 - 20 °C / Inert atmosphere 2.2: -75 - 20 °C | ||
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 8 h / 0 - 20 °C 2.1: n-butyllithium / cyclopentyl methyl ether / -75 - 20 °C / Inert atmosphere 2.2: 8 h / -75 - 20 °C / Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere; Darkness 2.1: n-butyllithium / cyclopentyl methyl ether / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 18 - 48 °C / Inert atmosphere 2.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0 - 20 °C 2.1: n-butyllithium / cyclopentyl methyl ether / -75 - 20 °C / Inert atmosphere 2.2: -75 - 20 °C 3.1: isopentyl nitrite / toluene / 80 - 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 8 h / 0 - 20 °C 2.1: n-butyllithium / cyclopentyl methyl ether / -75 - 20 °C / Inert atmosphere 2.2: 8 h / -75 - 20 °C / Inert atmosphere 3.1: toluene / 80 °C 3.2: 3 h / 80 - 110 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With triethylamine In chloroform at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere; Darkness 2.1: n-butyllithium / cyclopentyl methyl ether / 4 h / 0 - 20 °C / Inert atmosphere 2.2: 18 - 48 °C / Inert atmosphere 2.3: Inert atmosphere 3.1: isopentyl nitrite / toluene / 1.5 h / 95 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With fluorosulphonic acid In dichloromethane-d2; fluorosulfonylchloride at -78℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran; water / 12 h / 20 °C 2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate / N,N-dimethyl-formamide / 12 h / 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran; water / 12 h / 20 °C 2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper(II) acetate monohydrate; oxygen / 1,2-dichloro-ethane / 36 h / 110 °C / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | In methanol at 20℃; for 93h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide; copper(l) iodide; 1,7-phenanthroline / o-xylene / 10 h / Inert atmosphere; Reflux 2: copper(l) iodide; 1,7-phenanthroline; potassium carbonate / 1,2-dichloro-benzene / 10 h / Inert atmosphere; Reflux 3: sodium t-butanolate; palladium diacetate; XPhos / toluene / 10 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; copper(l) iodide; 1,7-phenanthroline / o-xylene / 10 h / Inert atmosphere; Reflux 2: copper(l) iodide; 1,7-phenanthroline; potassium carbonate / 1,2-dichloro-benzene / 10 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With copper(l) iodide; 1,7-phenanthroline; potassium hydroxide In o-xylene for 10h; Inert atmosphere; Reflux; | Synthesis of Intermediate 1-1 In a flask was added 3-fluoranthene amine (22g, 0.1mol), iodobenzene (21g, 0.1mol), potassium hydroxide (8g, 0.2mol), copper iodide (2g), phenanthroline (2g ) and o-xylene 300ml, nitrogen was heated at reflux for 10 hours, cooled, filtered, concentrated and the crude product was purified by column chromatography to give 24g, 83% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With palladium diacetate; sodium t-butanolate; XPhos In toluene for 10h; Reflux; Inert atmosphere; | 3 Example 3 Synthesis of Compound 11-1 In a flask was added 3 fluoranthene amine (4.48,20 honor 1), 2-bromo-9,9-dimethyl-fluorene (5.448,201111111), sodium t-butoxide (3g, 30mmol) , palladium acetate (100mg), X-phos (200mg), toluene (100ml), was heated at reflux under nitrogen for 10 hours, cooled, the solvent was removed and the crude product purified by column chromatography to give the product 5.8g, 71% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With palladium diacetate; sodium t-butanolate; XPhos In toluene for 12h; Reflux; Inert atmosphere; | 1 Example 1 Synthesis of Compound 1 In a flask was added 3- fluoranthene amine (2 · 2g, lOmmol), 2- bromo-9,9-dimethyl-fluorene (8 · 2g, 30mmol), sodium tert-butoxide (3g, 30mmol), palladium acetate (100mg), X-phos (200mg), toluene (100ml), was heated at reflux under nitrogen for 10 hours, cooled and the solvent removed to give the product 5.2g crude product purified by column chromatography, a yield of 86% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / dichloromethane / 0 - 20 °C 2: copper(II) acetate monohydrate; potassium hydrogencarbonate / tetrahydrofuran / 10 h / 105 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; trichlorophosphate In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In tetrahydrofuran at 80℃; for 21h; Inert atmosphere; |