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[ CAS No. 1211-37-6 ] {[proInfo.proName]}

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Product Details of [ 1211-37-6 ]

CAS No. :1211-37-6 MDL No. :
Formula : C13H7Br2N Boiling Point : -
Linear Structure Formula :- InChI Key :MGAAUJYLQGQIOK-UHFFFAOYSA-N
M.W : 337.01 Pubchem ID :14490102
Synonyms :

Safety of [ 1211-37-6 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1211-37-6 ]

* 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 [ 1211-37-6 ]

[ 1211-37-6 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 260-94-6 ]
  • [ 1211-37-6 ]
YieldReaction ConditionsOperation in experiment
76% With benzyltrimethylazanium tribroman-2-uide In methanol Inert atmosphere;
70% With benzyltriethylammonium tribromide In methanol at 80℃; for 2h;
69% With benzyltriethylammonium tribromide In methanol for 16h; Reflux;
63% With benzyltriethylammonium tribromide In methanol at 80℃; for 2h; Heating / reflux; 3 6.29 g (35.1 mmol) of acridine and 31.6 g (70.2 mmol, 2 eq.) of the BTEABr3 obtained as described above were added with 700 ml of methanol, and refluxed under a temperature condition of 80° C. for 2 hours. After that, the mixture was cooled to room temperature (25° C.) and filtered. Half of the filtrate thus obtained was concentrated to obtain a precipitate. The precipitate was separated by filtration, and thoroughly washed with ethanol to obtain 2,7-dibromoacridine (yellow solid: a yield of 6.81 g and 63%) expressed by the general formula (75). The UV spectra of acridine and 2,7-dibromoacridine thus obtained are shown in FIGS. 10 and 11, respectively.The obtained 2,7-dibromoacridine was subjected to 1H NMR measurement, and the obtained result is shown below.1H NMR (DMSO) δ9.10 (s, 1H), 8.52 (s, 2H), 8.11 (d, J=9.32 Hz, 2H), 7.99 (d, J=9.32 Hz, 2H).
With tetrachloromethane; N-Bromosuccinimide; dibenzoyl peroxide
Multi-step reaction with 3 steps 1.1: sulfuric acid; nitric acid / 2 h / 0 - 5 °C 2.1: palladium on activated charcoal; hydrogen / ethanol / 24 h / 20 °C 3.1: sulfuric acid; sodium nitrite; acetic acid / 2 h / 5 - 8 °C / Inert atmosphere 3.2: 2 h / 20 - 64 °C

  • 3
  • [ 1271-47-2 ]
  • [ 1211-37-6 ]
  • [ 503060-98-8 ]
YieldReaction ConditionsOperation in experiment
61% With PdCl2(PPh3)2; CuI In further solvent(s) soln. of Fe-complex, ligand and Pd-complex/CuI in diisopropylamine was heated under reflux for 15 h; extd. with CH2Cl2, washed with water, treated with MgSO4, column chromy.with CH2Cl2, silica plates with hexane-CH2Cl2-EtOAc; elem. anal.;
  • 4
  • [ 1271-47-2 ]
  • [ 1211-37-6 ]
  • [ 503061-01-6 ]
YieldReaction ConditionsOperation in experiment
26% With PdCl2(PPh3)2; CuI In further solvent(s) soln. of Fe-complex, ligand and Pd-complex/CuI in diisopropylamine was heated under reflux for 15 h; solvent was removed in vacuo, CH2Cl2 was added, extd. with CH2Cl2, washed with water, treated with MgSO4, column chromy. with CH2Cl2, silica plates with hexane-CH2Cl2-EtOAc;
  • 5
  • [ 1211-37-6 ]
  • [ 998-30-1 ]
  • [ 930798-61-1 ]
YieldReaction ConditionsOperation in experiment
51% With tetra-(n-butyl)ammonium iodide; triethylamine In N,N-dimethyl-formamide at 0 - 80℃; for 2h; 3 Under a nitrogen atmosphere, a mixture of 4.1 g (13.4 mmol) of 2,7-dibromoacridine, 304 mg (0.801 mmol, 6 mol %) of [Rh(CH3CN)2(cod)]BF4, and 9.90 g (26.8 mmol, 2 eq.) of tetrabutylammoniumiodide was added with 160 mL of dimethylformamide (DMF) to obtain a mixed solution. Then, the mixed solution was added with 5.60 ml (40.2 mmol, 3 eq.) of triethylamine, and then was added dropwise with 4.95 ml (26.8 mmol, 2 eq.) of triethoxysilane under a temperature condition of 0° C. to obtain a suspension. Thereafter, the suspension thus obtained was stirred under a nitrogen atmosphere and a temperature condition of 80° C. for 2 hours. After the stirring, the DMF was removed with a vacuum pump, and the suspension was extracted with ether three times, filtered with celite, and concentrated to obtain a crude product (a yield of 4.78 g). The crude product thus obtained was dissolved in 120 ml of ether, and then purified by filtering the resultant through activated carbon (Kiriyama funnel, diameter: 5 cm, thickness: 1.5 cm). Thereby, an acridine-silane compound was obtained (a red oily form: a yield of 3.44 g and 51%).The obtained acridine-silane compound was subjected to 1H NMR measurement. The obtained results are shown in FIGS. 12 to 14 and below. Moreover, the UV spectrum of the obtained acridine-silane compound is shown in FIG. 15.1H NMR (CDCL3) δ8.86 (s, 1H), 8.42 (s, 2H), 8.23 (d, J=8.64 Hz, 2H), 8.00 (d, J=8.64 Hz, 2H), 3.96 (q, J=7.02 Hz, 12H), 1.30 (t, J=7.02 Hz, 18H).Based on the NMR measurement results, it was confirmed that the acridine-silane compound obtained in Example 3 was an acridine-disilane compound expressed by the following general formula (88).
  • 6
  • [ 110-91-8 ]
  • [ 1211-37-6 ]
  • [ 1352136-09-4 ]
YieldReaction ConditionsOperation in experiment
65% With caesium carbonate; bis(dibenzylideneacetone)-palladium(0); XPhos In <i>tert</i>-butyl alcohol at 120℃; for 20h; Inert atmosphere;
  • 7
  • [ 1211-37-6 ]
  • [ 342002-80-6 ]
  • [ 1352136-16-3 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
  • 8
  • [ 1211-37-6 ]
  • [ 1352136-11-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine / toluene / 20 h / 130 °C / Inert atmosphere
  • 9
  • [ 1211-37-6 ]
  • [ 1352136-13-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine / toluene / 20 h / 130 °C / Inert atmosphere
  • 10
  • [ 1211-37-6 ]
  • [ 1352136-14-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; bis(dibenzylideneacetone)-palladium(0); XPhos / <i>tert</i>-butyl alcohol / 20 h / 120 °C / Inert atmosphere 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine / toluene / 20 h / 130 °C / Inert atmosphere
  • 11
  • [ 1211-37-6 ]
  • [ 1352135-97-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere 3: potassium hydroxide; potassium hexacyanoferrate(III) / dichloromethane; water / 20 h / 20 °C
  • 12
  • [ 1211-37-6 ]
  • [ 1352135-98-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere 3: potassium hydroxide; potassium hexacyanoferrate(III) / dichloromethane; water / 20 h / 20 °C
  • 13
  • [ 1211-37-6 ]
  • [ 1352135-99-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere 3: potassium hydroxide; potassium hexacyanoferrate(III) / dichloromethane; water / 20 h / 20 °C
  • 14
  • [ 1211-37-6 ]
  • [ 1352136-00-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere 3: potassium hydroxide; potassium hexacyanoferrate(III) / dichloromethane; water / 20 h / 20 °C
  • 15
  • [ 1211-37-6 ]
  • [ 1352136-01-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 100 °C / Inert atmosphere 3: potassium hydroxide; potassium hexacyanoferrate(III) / dichloromethane; water / 20 h / 20 °C
  • 16
  • [ 1211-37-6 ]
  • C36H41N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere
  • 17
  • [ 1211-37-6 ]
  • C30H23F6N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere
  • 18
  • [ 1211-37-6 ]
  • C36H37NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere
  • 19
  • [ 1211-37-6 ]
  • C34H37NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 70 °C / Inert atmosphere
  • 20
  • [ 1211-37-6 ]
  • C28H21F4N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: toluene / 20 h / 100 °C / Inert atmosphere
  • 21
  • [ 1211-37-6 ]
  • [ 128796-39-4 ]
  • [ 1352136-15-2 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
  • 22
  • [ 1211-37-6 ]
  • [ 156545-07-2 ]
  • [ 1352136-17-4 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
  • 23
  • [ 1211-37-6 ]
  • [ 145240-28-4 ]
  • [ 1352136-06-1 ]
  • 24
  • [ 1211-37-6 ]
  • [ 172975-69-8 ]
  • [ 1352136-07-2 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
  • 25
  • [ 1211-37-6 ]
  • [ 172975-69-8 ]
  • [ 1352136-12-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine / toluene / 20 h / 130 °C / Inert atmosphere
  • 26
  • [ 1211-37-6 ]
  • 3-isopropyloxyphenylboronic acid [ No CAS ]
  • [ 1352136-08-3 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
  • 27
  • [ 1211-37-6 ]
  • [ 98-80-6 ]
  • [ 1352136-05-0 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water Reflux;
  • 28
  • [ 1211-37-6 ]
  • [ 98-80-6 ]
  • [ 1352136-10-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane; water / Reflux 2: chloro(1,5-cyclooctadiene)rhodium(I) dimer; tricyclohexylphosphine / toluene / 20 h / 130 °C / Inert atmosphere
  • 29
  • [ 1211-37-6 ]
  • [ 99769-19-4 ]
  • dimethyl 3,3'-(acridine-2,7-diyl)dibenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane for 96h; Inert atmosphere; Reflux; Schlenk technique;
  • 30
  • [ 1211-37-6 ]
  • 5,5'-(acridine-2,7-diyl)diisophthalic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / 1,2-dimethoxyethane / 72 h / Inert atmosphere; Reflux; Schlenk technique 2: sodium hydroxide / water; methanol; tetrahydrofuran / 50 °C
  • 31
  • [ 1211-37-6 ]
  • [ 1309982-02-2 ]
  • tetraethyl 5,5'-(acridine-2,7-diyl)diisophthalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane for 72h; Inert atmosphere; Reflux; Schlenk technique;
  • 32
  • [ 1211-37-6 ]
  • 2,7-diiodoacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
23% With copper(l) iodide; potassium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide at 155℃; for 72h; Inert atmosphere; Synthesis of 2,7-diiodoacridine (3) A mixture of 2,7-dibromoacridine (2) (337 mg, 1.00 mmol), KI(5.01 g, 30.2 mmol), and CuI (1.90 g, 9.97 mmol) in HMPA(10 mL) was stirred at 155 C for 72 h. After the reaction mixturewas cooled to room temperature, 100 mL of water was added.Brown precipitate was collected and then Soxhlet extraction withtoluene gave pale brown solid. Crystallization of crude solid fromethyl acetate gave yellow powder of 3 (101 mg, 23%). 1H NMR(400 MHz, DMSO-d6): d 8.99 (s, 1H), 8.68 (d, J = 2.0 Hz, 2H), 8.08(dd, J = 9.2, 2.0 Hz, 2H), 7.92 (d, J = 9.2 Hz, 2H); MS (EI): m/z = 443[M]+. Anal for C13H7NI2, C; 36.23, H; 1.64, N; 3.25; found, C;36.05, H; 1.65, N; 3.13.
  • 33
  • [ 1211-37-6 ]
  • [ 1066-54-2 ]
  • 2,7-bis(ethynyltrimethylsilane)acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: 2,7-dibromoacridine With copper(l) iodide; triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) for 0.25h; Inert atmosphere; Stage #2: trimethylsilylacetylene at 75℃; Inert atmosphere; Darkness;
  • 34
  • [ 1211-37-6 ]
  • 2,7-diethynylacridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: copper(l) iodide; bis(dibenzylideneacetone)-palladium(0); triethylamine; triphenylphosphine / 0.25 h / Inert atmosphere 1.2: 75 °C / Inert atmosphere; Darkness 2.1: potassium hydroxide / methanol; water / 2 h / 20 °C / Inert atmosphere; Darkness
  • 35
  • [ 1211-37-6 ]
  • C39H39N7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: copper(l) iodide; bis(dibenzylideneacetone)-palladium(0); triethylamine; triphenylphosphine / 0.25 h / Inert atmosphere 1.2: 75 °C / Inert atmosphere; Darkness 2.1: potassium hydroxide / methanol; water / 2 h / 20 °C / Inert atmosphere; Darkness 3.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 16 h / 20 °C / Inert atmosphere; Darkness
  • 36
  • [ 1211-37-6 ]
  • C41H45N7(2+)*2F6P(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: copper(l) iodide; bis(dibenzylideneacetone)-palladium(0); triethylamine; triphenylphosphine / 0.25 h / Inert atmosphere 1.2: 75 °C / Inert atmosphere; Darkness 2.1: potassium hydroxide / methanol; water / 2 h / 20 °C / Inert atmosphere; Darkness 3.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 16 h / 20 °C / Inert atmosphere; Darkness 4.1: dichloromethane / 20 °C / Inert atmosphere; Darkness 4.2: PF6--loaded Amberlite®
  • 37
  • [ 23043-63-2 ]
  • [ 1211-37-6 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 3,6-diaminoacridine With sulfuric acid; acetic acid; sodium nitrite at 5 - 8℃; for 2h; Inert atmosphere; Stage #2: With hydrogen bromide; copper(I) bromide In water at 20 - 64℃; for 2h; 1 Synthesis of Intermediate B-15-1 A three-necked flask equipped with a thermometer was charged with 1.1 equivalents of NaNO2, concentrated sulfuric acid, and lowered to 2 ° C under nitrogen protection. A mixture of 2,7-diaminoacridine (3.14 g, 15 mmol)Dissolved in glacial acetic acid,Slowly added dropwise to the above mixture, and then reacted at 5-8 ° C for 2 h.Then cooled to -5 ° C, a large amount of ether was added and stirring was continued at -5 ° C for 25 min.The resulting filter cake was washed with ether. The resulting solid was added with CuBr and 48% aqueous HBr at room temperature, refluxed at 64 ° C for 2 h,The resulting solid was filtered, washed with deionized water and dried. The resulting crude product was passed through a silica gel column to give compound B-15-1 (2.67 g, 85%).
  • 38
  • [ 50-00-0 ]
  • [ 1211-37-6 ]
  • [ 85598-40-9 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: formaldehyd; 2,7-dibromoacridine With hydrogenchloride In 1,4-dioxane at 20℃; for 18h; Reflux; Stage #2: With sodium 2-nitropropane In ethanol; dimethyl sulfoxide for 3h; Inert atmosphere; 7 Synthesis of intermediate C-15-2 The reactor was charged with HCl (35.0 to 37.0%, 20 mL) and 1,4-dioxane (120 mL)(15.16 g, 45 mmol) and paraformaldehyde (4.0 g, 113 mmol) were added and stirred at reflux for 2 h. ThenAfter stirring at room temperature for 16 h. After completion of the reaction with water, the organic layer was separated with methylene chloride and dried over MgSO4. The solvent was removed by distillation under reduced pressureAnd the organic layer was separated by silica gel column chromatography to obtain a compound2,7-dibromo-9-chloroacridine(13.61 g, 81%).Under nitrogen conditions, 2,7-dibromo-9-chloroacridine (6.76 g, 18.2 mmol), DMSO (21 mL) was added to the reaction vessel,Stir for 30 min.Sodium (0.5 g, 21.7 mmol)Dissolved in ethanol,Add nitropropane for 3 h. The resulting substance is added to the DMSO counterStir in the system for 3h. After the end of the reaction, the solid material was filtered and the filtrate was extracted with water and extracted with dichloromethanePressure distillation gave compound C-15-2 (3.19 g, 48%).
  • 39
  • [ 79110-24-0 ]
  • [ 1211-37-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium on activated charcoal; hydrogen / ethanol / 24 h / 20 °C 2.1: sulfuric acid; sodium nitrite; acetic acid / 2 h / 5 - 8 °C / Inert atmosphere 2.2: 2 h / 20 - 64 °C
  • 40
  • [ 1211-37-6 ]
  • C45H27BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 3: N-Bromosuccinimide / dichloromethane / 5 h / 0 °C / Darkness
  • 41
  • [ 1211-37-6 ]
  • C48H34N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 3: N-Bromosuccinimide / dichloromethane / 5 h / 0 °C / Darkness 4: palladium diacetate / ethanol; toluene / 6 h / 100 °C
  • 42
  • [ 1211-37-6 ]
  • C24H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane / 18 h / 20 °C / Reflux 1.2: 3 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C
  • 43
  • [ 1211-37-6 ]
  • C48H32N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane / 18 h / 20 °C / Reflux 1.2: 3 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 3.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 12 h / 60 °C / Inert atmosphere
  • 44
  • [ 1211-37-6 ]
  • C60H40N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogenchloride / 1,4-dioxane / 18 h / 20 °C / Reflux 1.2: 3 h / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 3.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 12 h / 60 °C / Inert atmosphere 4.1: sodium metabisulfite / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux
  • 45
  • [ 1211-37-6 ]
  • [ 1214-21-7 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride; formaldehyd; water In 1,4-dioxane at 20℃; for 18h; Reflux; 7 Synthesis of Intermediate C-15-2 The reactor was charged with HCl (35.0 to 37.0%, 20 mL) and 1,4-dioxane (120 mL)(15.16 g, 45 mmol) and paraformaldehyde (4.0 g, 113 mmol) were added and stirred at reflux for 2 h. ThenAfter stirring at room temperature for 16 h. After completion of the reaction with water, the organic layer was separated with methylene chloride and dried over MgSO4. The solvent was removed by distillation under reduced pressureThe organic layer was separated by silica gel column chromatography to give the compound 2,7-dibromo-9-chloroacridine (13.61 g, 81%).Under nitrogen conditions, 2,7-dibromo-9-chloroacridine (6.76 g, 18.2 mmol), DMSO (21 mL) was added to the reaction vessel,Stir for 30 min. Sodium (0.5 g, 21.7 mmol) was dissolved in ethanol and nitropropane was stirred for 3 h. The resulting substance is added to the DMSO counterStir in the system for 3h. After the end of the reaction, the solid material was filtered and the filtrate was extracted with water and extracted with dichloromethanePressure distillation gave compound C-15-2 (3.19 g, 48%).
  • 46
  • [ 1211-37-6 ]
  • C45H28N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; toluene / 3 h / 120 °C
  • 47
  • [ 854952-58-2 ]
  • [ 1211-37-6 ]
  • C31H19BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 120℃; for 3h; 1 Synthesis of Intermediate B-15-2 Reaction container RigaN-phenyl-3-carbazole boronic acid (4.85 g, 16.9 mmol)B-15-1 (2.71 g, 8.05 mmol),Tetraphenylphenylphosphine palladium (0.7 g, 1.08 mmol)Potassium carbonate (5.3 g, 38.3 mmol), toluene (60 mL)20 mL of ethanol and 20 mL of distilled water were added and stirred at 120 ° C for 3 h.After the completion of the reaction, the reaction was stopped with distilled water and extracted with ethyl acetate.The organic layer was dried over MgSO4. After removal of the solvent by distillation under reduced pressure, the compound B-15-2 (5.49 g, 65%) was purified by silica gel column chromatography.
  • 48
  • [ 1211-37-6 ]
  • [ 75-26-3 ]
  • 2,7-diisopropyl acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 2,7-dibromoacridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: isopropyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 5h; 3 Preparation of intermediate (D-4) The reaction vessel was filled 1,6-diisopropyl-3,8-dibromopyrene (16.85 g, 50 mmol)Dimethylformamide (50 mL),Sodium hydride (4.40 g, 110 mmol / 60%) was added under nitrogen and at 0 ° CStir for 30 minutes,Additional 2-bromopropane (1.4 g, 2.16 mmol),Stir at room temperature for 5h.After completion of the reaction, the reaction mixture was quenched with ethyl acetate.The organic layer is dried over MgSO4.The solvent was distilled off under reduced pressure and then purified on a silica gel column to give Compound D-4 (12.20 g, 85%).
  • 49
  • [ 1211-37-6 ]
  • C19H20BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 5 h / 20 °C 2.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
  • 50
  • [ 1211-37-6 ]
  • C19H22BNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 5 h / 20 °C 2.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 3.1: tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere; Cooling
  • 51
  • [ 1211-37-6 ]
  • C60H60N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 5 h / 20 °C 2.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere 3.1: tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere 3.2: 2 h / Inert atmosphere; Cooling 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / ethanol; water; toluene / 3 h / 120 °C
  • 52
  • [ 1211-37-6 ]
  • [ 1692-15-5 ]
  • [ 2848574-90-1 ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis-(triphenylphosphine)-palladium; caesium fluoride at 90℃; for 72h; Inert atmosphere; 2.2 Combine 2,7-dibromoacridine (0.67 mg, 2.0 mmol),Pyridine-4-boronic acid (0.59 g, 2.4 mol), CsF (2.8 g, 18 mmol) and Pd(PPh3)4 (0.130 g, 0.12 mmol) were dissolved in dimethoxymethane (40 mL),Stir at 90°C for 3 days under N2 atmosphere. and by chromatography (methanol/chloroform = 1:50)The crude product was purified to give a yellow powder (0.3 g, 45% yield).
Same Skeleton Products
Historical Records

Related Parent Nucleus of
[ 1211-37-6 ]

Acridines

Chemical Structure| 4357-57-7

[ 4357-57-7 ]

9-Bromoacridine

Similarity: 0.93