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[ CAS No. 1714-27-8 ] {[proInfo.proName]}

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Product Details of [ 1714-27-8 ]

CAS No. :1714-27-8 MDL No. :MFCD16660390
Formula : C16H9Br Boiling Point : -
Linear Structure Formula :- InChI Key :FQVOKXARZCJTIT-UHFFFAOYSA-N
M.W : 281.15 Pubchem ID :3014034
Synonyms :

Safety of [ 1714-27-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1714-27-8 ]

* 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 [ 1714-27-8 ]

[ 1714-27-8 ] Synthesis Path-Downstream   1~83

  • 2
  • [ 1714-27-8 ]
  • [ 78751-58-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; ethyl bromide; dihydrogen peroxide; magnesium; diborane 1.) THF, reflux, 2 h, 2.) reflux, overnight, 3.) reflux, 30 min; Yield given. Multistep reaction;
  • 3
  • [ 1714-27-8 ]
  • [ 138181-89-2 ]
YieldReaction ConditionsOperation in experiment
With magnesium; ethylene dibromide In tetrahydrofuran 1) reflux, 2) r.t.;
  • 4
  • [ 129-00-0 ]
  • [ 1714-27-8 ]
YieldReaction ConditionsOperation in experiment
96% With N-Bromosuccinimide In chloroform at 15 - 20℃; for 24h;
80% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3h; 1 (1) Synthesis of 2-pyrenyl phenol 1) Synthesis of 2-pyrenyl phenol4.0 g (20 mmol) of pyrene,And 3.6 g (20 mmole) of N-bromosuccinimide.Was dissolved in dimethylformamide solution and reacted at room temperature for 3 hours.The organic layer was extracted from the toluene / water mixed solution, and then, using a silica gel chromatography tube,Purification yielded 4.5 g (80%) of 2-bromopyrene.2-bromopyrene (11 mmol), 2-anisoleboronic acid (10 mmol), potassium bicarbonate (33 mmol), and triethylamine were added to a mixed solution of toluene / water =[Tetra (triphenylphosphine)] palladium (5 mol%)And Xantphos (15 mol%) were added and reflux reaction was carried out for 12 hours.After the reaction, the solution was filtered, and the solvent was removed. Using a silica gel chromatography tube,Purification yielded 8.1 mmol (81%) of 2-pyrenyl anisole.The obtained 2-pyrenyl anisole (8 mmol)And tribromoboron (8.8 mmol,Dichloromethane 1M solution) was added to a dichloromethane solvent and stirred at room temperature for 12 hours.After the reaction, a water / dichloromethane mixed solution was added,The reaction product is extracted into an organic layer.The remaining water was removed with magnesium sulfate, and the residue was purified by silica gel chromatographyPurification yielded 6.9 mmol (86%) of 2-pyrenyl phenol.
Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / hexane / 16 h / 80 °C / Inert atmosphere 2: copper(ll) bromide / methanol; water / 16 h / 90 °C
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 24h; 3-1 (3-1) Synthesis of 1-bromopyrene (PLC-1) As shown in FIG. 4A, a solution of N-bromosuccinamide (4) (0.92g, 5.19 mmol, 1.05 eq) dissolved in dry DMF (20 mL) was dried. It was added to a solution of pyrene (3) (1.0 g, 4.94 mmol, 1.0 equivalent) dissolved in DMF (30 mL), and stirred at room temperature for 24 hours. After the reaction, the mixture was poured into water (50 mL) and extracted with dichloromethane (100 mL). The extract was washed well with water, dried over MgSO4, and evaporated under reduced pressure to give a pale yellow solid crude product, which was recrystallized from hexane to give 1-bromopyrene and PLC-1 as pale yellow powder

  • 5
  • [ 1714-27-8 ]
  • [ 115-19-5 ]
  • 2-(3-hydroxy-3-methyl-1-butynyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In various solvent(s)
YieldReaction ConditionsOperation in experiment
Tritrierung;
  • 8
  • [ 10549-27-6 ]
  • [ 1714-27-8 ]
YieldReaction ConditionsOperation in experiment
With o-tetrachloroquinone In benzene for 24h; Heating;
  • 10
  • 5-bromo-8-methoxy[2.2]metaparacyclophane-1,9-diene [ No CAS ]
  • [ 1714-27-8 ]
YieldReaction ConditionsOperation in experiment
90% With titanium tetrachloride In dichloromethane at 0℃; for 0.0166667h;
  • 11
  • [ 1714-27-8 ]
  • [ 292638-85-8 ]
  • methyl 3-(pyren-2-yl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate In 1-methyl-pyrrolidin-2-one at 130℃; for 13h;
  • 12
  • [ 1714-27-8 ]
  • [ 925201-12-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaHCO3 / (PPh3)2PdCl2 / 1-methyl-pyrrolidin-2-one / 13 h / 130 °C 2: H2 / Pd/C / tetrahydrofuran / 3.5 h / 2068.59 Torr
  • 13
  • [ 1714-27-8 ]
  • [ 925201-13-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaHCO3 / (PPh3)2PdCl2 / 1-methyl-pyrrolidin-2-one / 13 h / 130 °C 2: H2 / Pd/C / tetrahydrofuran / 3.5 h / 2068.59 Torr 3: KOSiMe3 / diethyl ether / 20 h / 20 °C
  • 14
  • [ 1714-27-8 ]
  • C40H48N7O17P3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaHCO3 / (PPh3)2PdCl2 / 1-methyl-pyrrolidin-2-one / 13 h / 130 °C 2: H2 / Pd/C / tetrahydrofuran / 3.5 h / 2068.59 Torr 3: KOSiMe3 / diethyl ether / 20 h / 20 °C 4: NaHCO3; Et3N; ethyl chloroformate / tetrahydrofuran; H2O / 0.17 h
  • 15
  • [ 129-00-0 ]
  • [ 1714-27-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2 / Pd/C / ethyl acetate / 192 h / 20 °C / 3102.89 Torr 2: Br2 3: o-chloranil / benzene / 24 h / Heating
  • 16
  • [ 1714-27-8 ]
  • [ 146445-96-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / KOH / methanol / 1 h / 20 °C
Multi-step reaction with 2 steps 1: 63 percent / CuI, (Ph3P)2PdCl2 / various solvent(s) 2: 50 percent / NaH / toluene
  • 17
  • [ 1714-27-8 ]
  • [ 62-53-3 ]
  • [ 81156-62-9 ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In toluene at 85℃; for 2h; 1.1 1) Synthesis of Intermediate I-1 2-Bromopyrene (synthesized by methods known in the literature. References: Chem. Eur. J. 2012, 18, 5022-5035) 1.41 g (5 mmol), aniline 0.93 g (10 mmol), Pd2 (dba) 3 0.09 g (0.1 mmol), PtBu3 0.02 g (0.1 mmol) and KOtBu 0.56 g (5.0 mmol) were dissolved in 50 mL of toluene and stirred at 85°C for 2 hours. After the reaction solution was cooled to room temperature, it was extracted three times with 50 mL of water and 50 mL of diethyl ether. The collected organic layer was dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified through silica gel tube chromatography to obtain 1.25 g (yield 85%) of intermediate I-1.
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 24h; 1.1 In a three-neck-round floor flask of 250 ml, after 127.5 m mole of aniline, 102 m mole of 2-bromopyrene, 1.53 m mole of tris(dibenzyllidene acetone)dipalladium, 3.06 m mol of BINAP(2,2'-bis(disphenylphosphino)-1,1'-binaphthyl, and 132.6 m mole of sodium-tert-butoxide were melted in 100 mL of toluene and they were mixed for 24 hours in a bath of 1000, when a reaction was terminated, toluene was removed from a reaction mixture and then the reaction mixture was extracted using dichloromethane and water and distilled under a reduced pressure, a solvent of a solution passing through a silica gel column was distilled under a reduced pressure, and thus 5.5 g of an N-phenylpyrene-2-amine liquid was obtained.
  • 19
  • dimesitylboron fluoride [ No CAS ]
  • [ 1714-27-8 ]
  • [ 1327238-65-2 ]
YieldReaction ConditionsOperation in experiment
31% Stage #1: 2-Bromopyrene With n-butyllithium In diethyl ether; hexane at -78 - 20℃; for 1h; Inert atmosphere; Stage #2: dimesitylboron fluoride In diethyl ether; hexane at -78 - 20℃; for 16h; Inert atmosphere;
  • 20
  • [ 4897-84-1 ]
  • [ 1714-27-8 ]
  • [ 1379589-21-5 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: Methyl 4-bromobutyrate With iodine; zinc In N,N-dimethyl-formamide at 70℃; for 16h; Inert atmosphere; Stage #2: 2-Bromopyrene With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;
  • 21
  • [ 1714-27-8 ]
  • [ 84679-52-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: iodine; zinc / N,N-dimethyl-formamide / 16 h / 70 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 20 °C
  • 22
  • [ 1714-27-8 ]
  • [ 1388771-59-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: sodium methylate; methanol / tetrahydrofuran / 12 h / Inert atmosphere 3.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: trifluoroacetic acid; benzenesulfonic acid / dichloromethane / 12 h / Inert atmosphere; Reflux 3.1: sodium methylate; methanol / tetrahydrofuran / 12 h / Inert atmosphere 4.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
  • 23
  • [ 1714-27-8 ]
  • [ 1401354-68-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: sodium methylate; methanol / tetrahydrofuran / 12 h / Inert atmosphere 3.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 5 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: trifluoroacetic acid; benzenesulfonic acid / dichloromethane / 12 h / Inert atmosphere; Reflux 3.1: sodium methylate; methanol / tetrahydrofuran / 12 h / Inert atmosphere 4.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
  • 24
  • [ 1714-27-8 ]
  • [ 1401354-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: trifluoroacetic acid; benzenesulfonic acid / dichloromethane / 12 h / Inert atmosphere; Reflux
  • 25
  • [ 1714-27-8 ]
  • [ 1401354-67-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: sodium methylate; methanol / tetrahydrofuran / 12 h / Inert atmosphere
Multi-step reaction with 3 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1.5 h / 55 °C / Inert atmosphere 1.2: 0 - 45 °C / Inert atmosphere 1.3: 2 h / 55 °C / Inert atmosphere 2.1: trifluoroacetic acid; benzenesulfonic acid / dichloromethane / 12 h / Inert atmosphere; Reflux 3.1: sodium methylate; methanol / tetrahydrofuran / 12 h / Inert atmosphere
  • 26
  • [ 1714-27-8 ]
  • [ 4330-21-6 ]
  • [ 1401354-65-1 ]
  • [ 1401354-66-2 ]
YieldReaction ConditionsOperation in experiment
1: 58% 2: 15% Stage #1: 2-Bromopyrene With magnesium; ethylene dibromide In tetrahydrofuran at 55℃; for 1.5h; Inert atmosphere; Stage #2: With copper(l) iodide In tetrahydrofuran at 0 - 45℃; Inert atmosphere; Stage #3: 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride In tetrahydrofuran at 55℃; for 2h; Inert atmosphere;
  • 27
  • [ 1714-27-8 ]
  • [ 17997-47-6 ]
  • [ 1449760-59-1 ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 20h; Schlenk technique; Inert atmosphere;
  • 28
  • [ 1714-27-8 ]
  • N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester [ No CAS ]
  • [ 1535206-18-8 ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester With iodine; zinc In N,N-dimethyl-formamide at 70℃; for 0.25h; Inert atmosphere; Stage #2: 2-Bromopyrene With tri(O-methylphenyl)phosphite; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 20 - 50℃; Inert atmosphere;
  • 29
  • [ 1714-27-8 ]
  • [ 1535206-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: zinc; iodine / N,N-dimethyl-formamide / 0.25 h / 70 °C / Inert atmosphere 1.2: 20 - 50 °C / Inert atmosphere 2.1: trifluoroacetic acid / chloroform-d1 / 1 h / 20 °C 3.1: triethylamine / chloroform / 18 h / 70 °C
  • 30
  • [ 1714-27-8 ]
  • C20H17NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: zinc; iodine / N,N-dimethyl-formamide / 0.25 h / 70 °C / Inert atmosphere 1.2: 20 - 50 °C / Inert atmosphere 2.1: trifluoroacetic acid / chloroform-d1 / 1 h / 20 °C
  • 31
  • [ 1714-27-8 ]
  • [ 33513-42-7 ]
  • [ 26933-87-9 ]
YieldReaction ConditionsOperation in experiment
3.5 g Stage #1: 2-Bromopyrene With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -78℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; diethyl ether; hexane at -30 - 20℃; for 16h;
  • 32
  • [ 1714-27-8 ]
  • 2'-O-(pyren-2-yl)methyluridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 2 h / -78 °C 1.2: 16 h / -30 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C 3.1: borane-THF; sodium hydrogencarbonate / dimethyl sulfoxide / 3 h / 140 °C / Inert atmosphere; Sealed tube
  • 33
  • [ 1714-27-8 ]
  • 5'-O-(4,4'-dimethoxytrityl)-2'-O-(pyren-2-yl)methyluridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 2 h / -78 °C 1.2: 16 h / -30 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C 3.1: borane-THF; sodium hydrogencarbonate / dimethyl sulfoxide / 3 h / 140 °C / Inert atmosphere; Sealed tube 4.1: pyridine; dmap / 14 h / 20 °C / Inert atmosphere
  • 34
  • [ 1714-27-8 ]
  • 3'-O-(2-cyanoethoxy(diisopropylamino)phosphinyl)-5'-O-(4,4'-dimethoxytrityl)-2'-O-(pyren-2-yl)methyluridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 2 h / -78 °C 1.2: 16 h / -30 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C 3.1: borane-THF; sodium hydrogencarbonate / dimethyl sulfoxide / 3 h / 140 °C / Inert atmosphere; Sealed tube 4.1: pyridine; dmap / 14 h / 20 °C / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
  • 35
  • [ 1714-27-8 ]
  • [ 24471-48-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; diethyl ether; hexane / 2 h / -78 °C 1.2: 16 h / -30 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 20 °C
  • 36
  • [ 1714-27-8 ]
  • 2-bromo-7-cyanopyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer / tetrahydrofuran / 80 °C / Schlenk technique; Inert atmosphere 2: cesium fluoride; copper(II) nitrate trihydrate / tetrahydrofuran; methanol; water / 100 °C
  • 37
  • [ 1714-27-8 ]
  • 2-cyano-7-(N,N-diethylamino)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(l) dimer / tetrahydrofuran / 80 °C / Schlenk technique; Inert atmosphere 2: cesium fluoride; copper(II) nitrate trihydrate / tetrahydrofuran; methanol; water / 100 °C 3: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium t-butanolate / 1,4-dioxane / 2 h / 120 °C / Schlenk technique; Inert atmosphere
  • 38
  • [ 1714-27-8 ]
  • [ 73183-34-3 ]
  • 2-(7-bromopyren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With (1,5-cyclooctadiene)(methoxy)iridium(l) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; Schlenk technique; Inert atmosphere;
52% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; Sealed tube; Preparation of intermediate 2-(7-bromopyren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1-1) 2-bromopyrene (2.00 g, 7.1 mmol), bis (pinacolato) diborone (2.06g, 8.1mmol) in a Shrink reaction tube,4,4'-Ditetrabutyl-2,2'-bipyridine (24 mg, 0.089 mmol), 1.2 mol%), [Ir (COD) (μ-OMe)] 2 (27 mg, 0.041mmol, 0.6 mol %) And THF (20 mL). The tube was sealed with a PTFE piston and heated in an oil bath at 80 ° C. overnight. After removing the solvent in vacuo, silica chromatography (SiO2; 1: 4 CH2Cl2 / hexane) Separated to obtain compound 1-1 (1.50 g, 52%). The obtained compound was confirmed by LC-MS.
  • 39
  • [ 1714-27-8 ]
  • [ 109-89-7 ]
  • 2-(N,N-diethylamino)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In 1,4-dioxane at 120℃; for 4h; Schlenk technique; Inert atmosphere;
  • 40
  • [ 1714-27-8 ]
  • C20H19B2NO5 [ No CAS ]
  • C52H33NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 24h; Inert atmosphere; Reflux; 21 Example 21: Synthesis of Compound 21 2-bromopyrene 100mmol , eight membered nitrogen (or sulfur) heterocyclic boride intermediate 220mmol was added to a 1L three-necked flask, was dissolved in 400mL of toluene, was added under nitrogen tetrakistriphenylphosphine palladium 1.5mmol , 250mmol potassium carbonate, distilled water 100mL, the reaction was stirred at reflux for 24 hours, cooled to room temperature after completion of the reaction, liquid separation funnel over silica gel, washing, spin-dry, recrystallized, filtered, 76mmol obtain compound 21 as a white solid, yield 76% .
  • 41
  • [ 1714-27-8 ]
  • C52H73BO4 [ No CAS ]
  • C62H70O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Inert atmosphere;
  • 42
  • [ 1714-27-8 ]
  • 7-bromo-2-octylpyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium; iodine / diethyl ether / 45 °C 1.2: 12 h / Reflux 2.1: N-Bromosuccinimide; acetic acid / chloroform / 12 h / 20 °C
  • 43
  • [ 1714-27-8 ]
  • 7-carboxy-2-octylpyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium; iodine / diethyl ether / 45 °C 1.2: 12 h / Reflux 2.1: N-Bromosuccinimide; acetic acid / chloroform / 12 h / 20 °C 3.1: magnesium; iodine / diethyl ether
  • 44
  • [ 111-83-1 ]
  • [ 1714-27-8 ]
  • 2-(n-octyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-Bromopyrene With iodine; magnesium In diethyl ether at 45℃; Stage #2: 1-bromo-octane for 12h; Reflux; 1.1 1. 2.82 g of 2-bromopyrene was dissolved in 100 mL of dry diethyl ether,Then 0.5 g of magnesium bar and 0.1 g of iodine were added,Heated to 45 ° C to return to the magnesium completely dissolved;Cooled to room temperature,2 g of 1-bromooctane,And the mixture was heated under reflux for 12 hours.After the reaction, the mixture was cooled to room temperature,The ether was removed as a solvent by rotary evaporation,And then purified using a silica gel column,To give 2-octylpyrene.
  • 45
  • [ 1714-27-8 ]
  • [ 34907-53-4 ]
  • C36H28BN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / Inert atmosphere; Schlenk technique; Reflux 1.2: -78 - 20 °C / Inert atmosphere; Schlenk technique 2.1: n-butyllithium / diethyl ether / 1 h / -78 °C / Inert atmosphere; Schlenk technique 2.2: 18 h / -78 - 20 °C / Inert atmosphere; Schlenk technique
  • 46
  • [ 1714-27-8 ]
  • [ 34907-53-4 ]
  • C26H23BO [ No CAS ]
  • 47
  • [ 1714-27-8 ]
  • 1-(2-ethynylphenyl)hex-2-yn-1-ol [ No CAS ]
  • 1-(2-(pyren-2-ylethynyl)phenyl)hex-2-yn-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 2-Bromopyrene With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran Inert atmosphere; Schlenk technique; Stage #2: 1-(2-ethynylphenyl)hex-2-yn-1-ol In tetrahydrofuran for 3h; Schlenk technique; Inert atmosphere; Reflux;
  • 48
  • [ 1714-27-8 ]
  • C35H29BN2O2 [ No CAS ]
  • C45H26N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate at 90℃; for 48h; Inert atmosphere; 31.4 Example 10 Synthesis of Compound 10 General procedure: (4) A mixture of 9- (4-pinacol borate) -9 hydrogen-pyrene imidazole (6.46 g)9-bromoanthracene (3.08 g),Was added to a 250 mL round bottom flask,Add the newly prepared potassium carbonate solution (50 mL, 2 mol / L)Under N2 protection,The catalyst Pd (PPh3) 4 (0.69 g) was added to the system,The whole reaction system was then subjected to a Suzuki coupling reaction at 90 ° C,Reaction for 48 hours.After the end of the reaction to be cooled to room temperature,The reaction mixture was extracted with a small amount of distilled water and an appropriate amount of methylene chloride,The organic layer was collected and concentrated using a rotary evaporator,Finally, a white powder product was isolated by column chromatography on a silica gel column,Yield 81%.
  • 49
  • [ 1714-27-8 ]
  • C18H10N4 [ No CAS ]
  • C50H26N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 24h; Inert atmosphere; 19 Example 19: Synthesis of Compound 19 Under nitrogen protection,A solution of bipyrazole pyrene intermediate 101 mmol,2-bromopyrene 225 mmol,Tris (dibenzylideneacetone) dipalladium 5.1 mmol,Sodium tert-butoxide 411 mmol,Tri-tert-butylphosphine 20 mmol was placed in a reaction vessel,And dissolved in 500 ml of toluene,110 reflux reaction 24h,The reaction was carried out by thin layer chromatography (TLC). The reaction was completed, cooled to room temperature, passed through a silica gel funnel, washed with methylene chloride, spin dried, recrystallized from dichloromethane / petroleum ether,After drying, 80 mmol of compound 19 was obtained,Yield 80%.
  • 50
  • [ 1714-27-8 ]
  • C38H23N3OS [ No CAS ]
  • C54H31N3OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With potassium phosphate; copper(l) iodide In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Inert atmosphere; Reflux; 5 Under a nitrogen atmosphere, to a 500 ml three-necked flask, 56.9 g of compound U (100 mmol) and 30.3 g of compound V were added.(110 mmol), 7.6 g of cuprous iodide (40 mmol), 42.4 g of tripotassium phosphate (200 mmol), and 300 g of xylene, and the mixture was heated under reflux for 6 hours.TLC traces no compound U. After the reaction is complete, the temperature is reduced to 30° C., filtered, and the xylene 50 ml*3 is rinsed. The filtrate is washed with water 200 g*3 until pH=7. After drying, the silica gel column is subjected to atmospheric pressure. After the column is completed, xylene 50ml*2 is rinsed on the silica gel column, rinsed, and the elution solution is combined with the column liquid to desolventize the solvent. After desolventization, 500g of tetrahydrofuran and 200g of n-hexane are added to recrystallize three times and dried. 30.7 g of compound 76, yield: 40.0%, HPLC: 99.6%.
  • 51
  • [ 76-86-8 ]
  • [ 1714-27-8 ]
  • C34H24Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2-Bromopyrene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: Triphenylsilyl chloride In tetrahydrofuran at 20℃; for 1h; 1.1 Example 1: Preparation of Compound 1 Step1. Take 100mmol 2-bromopyrene,Add in anhydrous THF to dissolve,Cool down to -78 ° C,Add 1.5 equivalents of n-butyllithium,Reacting at this temperature for 2 hours,One equivalent of triphenylchlorosilane was added, and the temperature was gradually raised to room temperature, and the reaction was carried out for 1 hour. anti-After completion, it should be added, deionized water, the organic phase is extracted with EtOAc, the organic phase is dried, concentrated, and subjected to column chromatography to obtain a product.60mmol. The yield was 60%.
  • 52
  • [ 1714-27-8 ]
  • 9-(3-(chlorodiphenylsilyl)phenyl)-9H-carbazole [ No CAS ]
  • C46H31NSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2-Bromopyrene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: 9-(3-(chlorodiphenylsilyl)phenyl)-9H-carbazole In tetrahydrofuran at 20℃; for 1h; 2.3 Step3. Take 32mmol 2-bromopurine,Add in anhydrous THF to dissolve,Cool down to -78 ° C,Add 1.5 equivalents of n-butyl lithium,Reacting at this temperature for 2 hours,Add 1 equivalent of 3-2,Gradually warm to room temperature,The reaction was for 1 hour.Add after the reaction is completed,Deionized water,The organic phase was extracted with EtOAc.The organic phase is dry,concentrate,Column chromatography,The product was obtained in 19.2 mmol.The yield was 60%.
  • 53
  • [ 1714-27-8 ]
  • 3-(9H-carbazol-9-yl)benzenethiol [ No CAS ]
  • C34H21NS [ No CAS ]
YieldReaction ConditionsOperation in experiment
40 mmol With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux; 3.3 Step3. Add 19-2 50mmol to the reaction vessel.2-bromoindole 50mmol,Potassium tert-butoxide 150mmol,Pd2 (dba)3 0.5mmol,Ultrasonic deoxygenated xylene,Stir and dissolve,Replace the air three times,Adding ligand tri-tert-butylphosphine 4% (2mmol, 50% m/V),Replace the air three times,The reaction was refluxed for 6 h.Cool to room temperature,Add enough dichloromethane to completely dissolve the product.a small amount of silica gel funnel,Remove catalyst and salt.The filtrate is concentrated to a viscous state.Column chromatography,The product 19-3 40 mmol was obtained.
  • 54
  • [ 1714-27-8 ]
  • [ 1079-66-9 ]
  • diphenyl(pyren-1-yl)phosphane [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 2-Bromopyrene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: chloro-diphenylphosphine In tetrahydrofuran at 20℃; for 1h; 4.1 Example 4: Preparation of Compound 33 Step1. Take 100mmol 2-bromoindole,Add in anhydrous THF to dissolve,Cool down to -78 ° C,Add 1.5 equivalents of n-butyl lithium,Reacting at this temperature for 2 hours,Add 1 equivalent of diphenylphosphonium chloride,Gradually warm to room temperature,The reaction was for 1 hour.After the reaction is completed, the mixture is deionized water, the organic phase is extracted with EtOAc, the organic phase is dried, concentrated, and then purified to afford product 33-180mmol. The yield was 80%.
  • 55
  • [ 1714-27-8 ]
  • 2-(pyren-2-yl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydrogencarbonate; triethylamine; tetrakis(triphenylphosphine) palladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene; water / 12 h / Reflux 2: boron tribromide / dichloromethane / 12 h / 20 °C
  • 56
  • [ 1714-27-8 ]
  • [ 5720-06-9 ]
  • 2-pyrenylanisole [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(triphenylphosphine) palladium(0); potassium hydrogencarbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; toluene for 12h; Reflux; 1 Example 1 1) Synthesis of 2-pyrenyl phenol4.0 g (20 mmol) of pyrene,And 3.6 g (20 mmole) of N-bromosuccinimide.Was dissolved in dimethylformamide solution and reacted at room temperature for 3 hours.The organic layer was extracted from the toluene / water mixed solution, and then, using a silica gel chromatography tube,Purification yielded 4.5 g (80%) of 2-bromopyrene.2-bromopyrene (11 mmol), 2-anisoleboronic acid (10 mmol), potassium bicarbonate (33 mmol), and triethylamine were added to a mixed solution of toluene / water =[Tetra (triphenylphosphine)] palladium (5 mol%)And Xantphos (15 mol%) were added and reflux reaction was carried out for 12 hours.After the reaction, the solution was filtered, and the solvent was removed. Using a silica gel chromatography tube,Purification yielded 8.1 mmol (81%) of 2-pyrenyl anisole.The obtained 2-pyrenyl anisole (8 mmol)And tribromoboron (8.8 mmol,Dichloromethane 1M solution) was added to a dichloromethane solvent and stirred at room temperature for 12 hours.After the reaction, a water / dichloromethane mixed solution was added,The reaction product is extracted into an organic layer.The remaining water was removed with magnesium sulfate, and the residue was purified by silica gel chromatographyPurification yielded 6.9 mmol (86%) of 2-pyrenyl phenol.
  • 57
  • 1-amino-2-bromopyrene [ No CAS ]
  • [ 1714-27-8 ]
YieldReaction ConditionsOperation in experiment
88.5% Stage #1: 1-amino-2-bromopyrene With sulfuric acid for 0.5h; Stage #2: With sodium nitrite In water at 0 - 5℃; for 1.5h; Stage #3: With phosphinic acid In water at 0 - 5℃; 4; 1 1), 2-bromoindole synthesis: 1.1),Add a sulfuric acid solution (containing 1 mol of sulfuric acid) to a 1000 mL reaction flask.Add 148g of 1-amino-2-bromoindole (0.5mol,Prepared in Example 1),Stir for 30 minutes to dissolve all of them.Cool the solution to 0-5 ° C,At this point, solids will precipitate.Subsequent addition (control system temperature does not exceed 5 ° C during the addition process) sodium nitrite aqueous solution (containing sodium nitrite 0.5 mol),Control the reaction temperature at 0-5 ° C,After the drop,The reaction system will become clear,The temperature was controlled to stir at 0-5 ° C for 30 minutes.The diazonium salt solution was obtained for use.In this embodiment, a sulfuric acid solution (containing 1 mol of sulfuric acid) having a concentration of 2 g/10 mL is used.The concentration was 3.5 g/10 mL of an aqueous solution of sodium nitrite (containing sodium nitrite 0.5 mol).which is,a molar ratio of 1-amino-2-bromoindole: sulfuric acid (H2SO4) = 1:2;1-amino-2-bromoindole: sodium nitrite = 1:1 molar ratio.Note: In the above diazotization reaction, sulfuric acid reacts with sodium nitrite to form nitrous acid, and nitrous acid reacts with NH2 in 1-amino-2-bromoindole to form a diazonium salt.1.2),The diazonium salt solution prepared in the step 1.1) is slowly added dropwise to the mechanical stirring to reduce the temperature to 0-5 ° C.In the aqueous hypophosphorous acid solution (about 1 hour), a large amount of gas is released during the dropwise addition. After the addition is completed, at 0-5 ° CThe incubation reaction was carried out for about 30 minutes, monitored by HPLC, and the reaction was completed; the filter cake was dried by filtration and dried at 60 ° C.To constant weight), 130 g of 2-bromoindole was obtained.In this embodiment, a hypophosphorous acid aqueous solution (containing 2 mol of hypophosphorous acid) having a concentration of 2.5 g/10 mL is used;That is, 1-amino-2-bromoindole: hypophosphite = 1:4 molar ratio.2), 2-bromoindole purification: 130 g of the crude 2-bromoindole obtained in step 1), added to a 500 mL three-neck bottle, and then added2 times the weight of ethyl acetate, warmed to reflux, and then cooled to 20 ± 2 ° C to achieve crystallization, and finally the mixture was filtered,The crystallized body is dried (dried to constant weight at 80 ° C) to obtain pure 2-bromopurine (purity 99.9%), weight 115 g, yield88.5%, the HPLC chromatogram is shown in Figure 1.
  • 58
  • [ 34069-89-1 ]
  • [ 1714-27-8 ]
  • C32H23NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.6% With copper; potassium carbonate In 1,2-dichloro-benzene at 180℃; for 48h; Inert atmosphere; 8 Preparation method of compound of formula i24: 2.85 g (10 mmol) was added sequentially to a 250 mL round bottom flask.I23,3.37 g (12 mmol) of 2-bromoindole, 1.66 g (12 mmol) of potassium carbonate,0.13 g (2 mmol) of activated copper powder and 100 mL of o-dichlorobenzene,Degas the reaction system and then protect it with argon.The mixture was heated to 180 ° C with stirring and the reaction was continued for 48 h. After the reaction is complete,The system was cooled to room temperature, suction filtered under reduced pressure and the residue was washed with dichloromethane.After spinning the filtrate dry, use dichloromethane:The petroleum ether = 3:2 (volume ratio) eluent was separated and purified on a silica gel column.Get a dark yellow green solid3.96g,The yield was 81.6%.
  • 59
  • [ 1714-27-8 ]
  • [ 106-45-6 ]
  • pyren-2-yl(p-tolyl) sulfide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 2-Bromopyrene; para-thiocresol In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With sodium hydride In N,N-dimethyl-formamide for 10.1667h; Inert atmosphere; Reflux; 2.2.1. Synthesis of pyren-1-yl(p-tolyl)sulfide (1) General procedure: 1.69 g (12 mmol) 4-methylbenzenethiol, 2.81 g (10 mmol) 1-bromopyrene and 50 mL DMF were added into a 100ml roundbottom flask. The above mixture was stirred for 10 min in an icebath under the protection of N2. Then, 0.48 g (12 mmol) NaH (60%)was slowly added into the above flask in batches and the mixturewas stirred for another 10 min. After all the generated hydrogenwas discharged, the mixture was refluxed for 10 h, poured intowater, extracted with DCM and washed with water for three times.The organic phase was dried over MgSO4, filtered, and concentrated.The concentrated product was purified by silica gel flashcolumn chromatography using hexane as the eluent. Yield: 2.60 g,80%.
  • 60
  • [ 1714-27-8 ]
  • [ 5720-07-0 ]
  • 1-(4-methoxyphenyl)pyrene [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With tetraamminepalladium(II) chloride; tetra(n-butyl)ammonium hydroxide In water at 45℃; for 2h; Green chemistry;
  • 61
  • [ 1714-27-8 ]
  • [ 63006-66-6 ]
  • C50H31N [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In toluene at 85℃; for 4h; 1 Synthesis of Compound 4 2-bromopyrene 1.40 g (5.0 mmol), Intermediate I-4 1.23 g (5.0 mmol), Pd (dba) (Tris (dibenzylideneacetone) dipalladium (0)) 0.09 g (0.1 mmol), P t Bu 0.01 g(0.1 mmol) of (Tri-tert-butylphosphine) and 1.38 g (10.0 mmol) of KO t Bu were dissolved in 20 mL of toluene, followed by stirring at 85 ° C. for 2 hours. Thereaction solution was cooled to room temperature, and extracted three times with 20 mL of water and 20 mL of diethyl ether. The organic layer obtained was driedover magnesium sulfate, and the residue obtained by evaporation of the solvent was dissolved in 20 mL of toluene again, and 6.18 g (5.0 mmol) of 2-bromopyrene,0.09 g (0.1 mmol) of Pd (dba) obtained. , P t Bu 0.01 g (0.1 mmol) and KO t Bu 1.38 g (10.0 mmol) was added, followed by stirring at 85 ° C. for 2 hours.The reaction solution was cooled to room temperature, and extracted three times with 20 mL of water and 20 mL of diethyl ether. The resulting organic layer wasdried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified through silica gel column chromatography toobtain Compound 4 (2.74 g, 85% yield). The produced compound was confirmed by MS / FAB and H NMR.
  • 62
  • [ 1714-27-8 ]
  • C31H21Br [ No CAS ]
  • [ 62-53-3 ]
  • C53H35N [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 2-Bromopyrene; aniline With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In toluene at 85℃; for 2h; Stage #2: C31H21Br With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In toluene at 85℃; for 2h; 13 Synthesis of Compound 34 2-bromopyrene 1.40 g (5.0 mmol), aniline 0.46 g (5.0 mmol), Pd (dba) (Tris (dibenzylideneacetone) dipalladium (0)) 0.09 g (0.1 mmol), P t Bu (Tri- 0.01 g (0.1mmol) of tert-butylphosphine) and 1.38 g (10.0 mmol) of KO t Bu were dissolved in 20 mL of toluene, followed by stirring at 85 ° C. for 2 hours. The reactionsolution was cooled to room temperature, and extracted three times with 20 mL of water and 20 mL of diethyl ether. The organic layer obtained therefrom was driedover magnesium sulfate and the solvent was evaporated, and the residue obtained was dissolved in 20 mL of toluene again, and 2.36 g (5.0 mmol) of intermediateI-34, 0.09 g (0.1 mmol) of Pd (dba) , 0.01 g (0.1 mmol) P t Bu and KO t Bu 1.38 g (10.0 mmol) was added, followed by stirring at 85 ° C. for 2 hours. Thereaction solution was cooled to room temperature, and extracted three times with 20 mL of water and 20 mL of diethyl ether. The organic layer thus obtained wasdried over magnesium sulfate and the residue obtained by evaporation of the solvent was separated and purified through silica gel column chromatography toobtain Compound 34 (2.84 g, 83% yield). The produced compound was confirmed by MS / FAB and H NMR.
  • 63
  • [ 1714-27-8 ]
  • C68H47N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 5 h / 80 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C 2.2: 2 h / 85 °C
  • 64
  • [ 1714-27-8 ]
  • [ 5467-74-3 ]
  • [ 23801-23-2 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 5h; 2 Synthesis of Intermediate I-42 6.75 g (24.0 mmol) of 2-bromopyrene, 4.00 g (20.0 mmol) of 4-bromobenzene-1-boronic acid, 1.15 g (1.0 mmol) of Pd (PPh ) and 4.14 g (30.0 of K CO )mmol) was dissolved in 60 mL of a THF (tetrahydrofuran) / H 0 (2/1) mixed solution and stirred at 80 ° C. for 5 hours. The reaction solution was cooled to roomtemperature, and then extracted three times with 60 mL of water and 60 mL of diethyl ether. The organic layer thus obtained was dried over magnesium sulfate,and the residue obtained by evaporation of the solvent was separated and purified by silica gel column chromatography to obtain 5.43 g (76% yield) of IntermediateI-42. The resulting compound was confirmed by LC-MS.C
  • 65
  • [ 107955-86-2 ]
  • [ 1714-27-8 ]
  • C57H32O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium phosphate; tri-tert-butyl phosphine; palladium diacetate In toluene for 36h; Inert atmosphere; Reflux; 14 Synthesis Example 14 Preparation of Chiral Spiral Isomers M22R & M22S Weigh 346mg of (R) -2,2’-dihydroxy-9,9’-spirobifluorene and addIn a reaction tube containing 10 mL of toluene,Add 9mg of palladium acetate,425mg potassium phosphate,25mg tri-tert-butylphosphine to 700mg 2-Bromo-pyrene,Under nitrogen protection,Heating under reflux,After 36 hours of reaction,TCL detection of disappearance of raw materials,That is, the reaction is completed.The temperature drops to room temperature,Pour the reaction solution intoExtraction in ethyl acetate,The organic phase is dried over anhydrous sodium carbonate,Spin-dry the solvent,The product was separated by column chromatography,Yield 60% (0.45 g).
  • 66
  • [ 1714-27-8 ]
  • 4-(7-bromopyren-2-yl)-N,N-diphenylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating
  • 67
  • [ 1714-27-8 ]
  • N,N-diphenyl-4-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / toluene / 80 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating
Multi-step reaction with 4 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: copper(ll) bromide / tetrahydrofuran; methanol; water / 16 h / 90 °C 3: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / toluene / 80 °C / Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating
  • 68
  • [ 1714-27-8 ]
  • [ 102587-98-4 ]
  • 69
  • [ 1714-27-8 ]
  • 4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / toluene / 80 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: copper(ll) bromide / tetrahydrofuran; methanol; water / 16 h / 90 °C 3: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / toluene / 80 °C / Inert atmosphere
  • 70
  • [ 1714-27-8 ]
  • 4,4'-(pyrene-2,7-diyl)bis(N,N-diphenylaniline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / toluene / 80 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating
Multi-step reaction with 5 steps 1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 80 °C / Sealed tube 2: copper(ll) bromide / tetrahydrofuran; methanol; water / 16 h / 90 °C 3: tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; potassium acetate / toluene / 80 °C / Inert atmosphere 4: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating 5: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; toluene; ethanol / 15 h / Heating
  • 71
  • [ 1714-27-8 ]
  • C39H25BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C
  • 72
  • [ 1714-27-8 ]
  • C61H34(2)H5N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C 3: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C
  • 73
  • [ 1714-27-8 ]
  • C55H35N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C
  • 74
  • [ 1714-27-8 ]
  • C56H36N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C 2: tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate / toluene / 2 h / 85 °C
  • 75
  • [ 18471-73-3 ]
  • [ 1714-27-8 ]
  • C27H18N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In toluene at 85℃; for 2h; 8.1 1) Synthesis of Intermediate I-4 2-bromopyrene 1.41 g (5 mmol), 4-pyridin-2-yl-phenylamine 1.70 g (10 mmol), Pd2(dba)3 0.09 g (0.1 mmol), PtBu3 0.02 g (0.1 mmol) and KOtBu 0.56 g (5.0 mmol) was dissolved in 50 mL of toluene and stirred at 85° C. for 2 hours. The reaction solution was cooled to room temperature, and extracted three times with 50 mL of water and 50 mL of diethyl ether. The collected organic layer was dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified through silica gel tube chromatography to obtain 1.55 g (yield 84%) of Intermediate I-4.
  • 76
  • [ 4165-61-1 ]
  • [ 1714-27-8 ]
  • C22H10(2)H5N [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium <i>tert</i>-butylate In toluene at 85℃; for 2h; 8.3 3) Synthesis of Intermediate I-6 2-bromopyrene 1.41 g (5 mmol), aniline-2,3,4,5,6-d5 0.98 g (10 mmol), Pd2(dba)3 0.09 g (0.1 mmol), PtBu3 0.02 g (0.1 mmol) And 0.56 g (5.0 mmol) of KOtBu was dissolved in 50 mL of toluene, followed by stirring at 85°C for 2 hours. The reaction solution was cooled to room temperature, and extracted three times with 50 mL of water and 50 mL of diethyl ether. The collected organic layer was dried with magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography to obtain 1.25 g (yield 84%) of Intermediate I-6.
  • 77
  • [ 1714-27-8 ]
  • 4,4'-bis[(4-nitrophenyl)amine]-4"-isobutoxytriphenylamine [ No CAS ]
  • 4,4'-bis[4-nitrophenyl(2-pyrenyl)amine]-4”-isobutoxytriphenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.8% With 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; nickel; sodium carbonate at 160℃; for 24h; Inert atmosphere; 5 Add 4.00g (6.78mmol) 4,4'-bis[(4-nitrophenyl)amine]4"-isobutoxytriphenylamine into a 250mL three-necked flask equipped with a magnetic stir bar and condenser tube, 4.77g (16.96mmol) 2-bromopyrene, 3.18g (54.24mmoL) nickel, 5.75g (54.24mmoL) sodium carbonate, 1.82g (6.78mmoL) benzo-15-crown-5, add 15.7mL dichlorotoluene The solid content of the system is 30%. Under the protection of nitrogen, the reaction is carried out at 160°C for 24 hours. After the reaction is completed, it is filtered while hot, and methanol is added to the filtrate to precipitate solids. The resulting crude product is purified by column chromatography (developing solvent: dichloromethane) Petroleum ether=5:1) to obtain 4.36g of 4,4'-bis[4-nitrophenyl(2-pyrenyl)amine]-4”-isobutoxytriphenylamine as a red powder, with a yield of 64.8% .
  • 78
  • [ 1714-27-8 ]
  • 7,17-dimethyl-7,17-divinyl-1,3,5,9,11,13,15,1-octaphenylhexacyclo[9.13.11,9 .13,15 .15,13 .111,19 ]decasiloxane [ No CAS ]
  • C86H68O14Si10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With palladium diacetate; triethylamine; triphenylphosphine In toluene at 100℃; Inert atmosphere; 4-1 (4-1) Synthesis of DSQP-1 As shown in Figure 7a, in a dried flask (100 mL) V.DDSQ (1.0g, 0.83mmol, 1.0 equivalent), 1-bromopyrine (PLC-1), (1.41g, 4.98mmol, 6.0 equivalent) , Palladium (II) acetate (0.019g, 0.083mmol, 0.1 equivalent) and triphenylphosphine (0.044g, 0.17mmol, 0.2 equivalent) were added, followed by anhydrous toluene (20 mL) and triethylamine (1.0 mL) Was added and stirred vigorously and the flask was purged with nitrogen for 30 minutes. The reaction was carried out at 100° C., and the reaction progress was monitored by TLC at regular intervals. After 38 hours, the starting material (V.DDSQ) disappeared and a new spot was obtained at Rf=0.46. The reaction mixture is cooled to room temperature and filtered to obtain an insoluble solid (i.e., triphenylphosphine and acetic acid arm).The complex of radium (II)) was removed. The filtrate was concentrated with a rotary evaporator, added dropwise to methanol (10 mL) and dried to obtain a crude product, which was purified by silica gel chromatography using dichloromethane:hexane (1:3) to obtain a yellow solid (1.10 g, yield 78 %).
  • 79
  • [ 613-13-8 ]
  • [ 1714-27-8 ]
  • C30H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
62.3% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 120℃; for 10h; Inert atmosphere; 7.1 Step 1: Synthesis of Intermediate 83-1 The 2-aminoanthracene (15g, 77.6mmol), 7-bromo-1,9-dihydro (22g, 77.6mmol),Sodium tert-butoxide (14.9g, 155.2mmol) was added to the reaction flask and replaced with nitrogen 3 times.Add toluene (200ml) under nitrogen protection, replace with nitrogen 3 times, add tris(dibenzylideneacetone) bispalladium (0.7g, 0.776mmol), 50% tri-tert-butylphosphine (0.62g, 0.155mmol) under nitrogen protection , Nitrogen replacement 3 times, heating to 120°C and stirring for 10h.Cool to room temperature, add 100ml of water and stir for 30min, suction and filter to dry the solid,The solid compound was separated and purified by column chromatography to obtain 24.5 g of solid compound with a yield of 62.3%.
  • 80
  • [ 613-13-8 ]
  • [ 1714-27-8 ]
  • C60H37NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 10 h / 120 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri-tert-butyl phosphine / toluene / 10 h / 120 °C / Inert atmosphere
  • 81
  • [ 1714-27-8 ]
  • C25H24BrN3S [ No CAS ]
  • C41H33N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 2-Bromopyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: C25H24BrN3S In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere; Schlenk technique; 5.2 (2) Synthesis of target molecule BTZ-DMAc-C4-PYR Add PYR-Br (140 mg, 0.5 mmol) to a 100 mL Schlenk flask, and add 20 mL of tetrahydrofuran that has been dewatered and deoxygenated under an argon atmosphere. Then, while stirring at -78 °C, 1.6 mol/L n-butyl lithium n-hexane solution (n-BuLi in hexane, 0.32 mL, 0.5 mmol) was slowly added dropwise to it. After the addition is completed, stirring is continued for 2 hours at low temperature and then BTZ-DMAc-C4-Br (238 mg, 0.5 mmol) is added thereto, and then reacted at room temperature for 12 hours. The reaction was quenched with water, the reaction solution was poured into 50 mL ice water, extracted three times with dichloromethane, the organic phase was concentrated, and the column chromatography was separated (n-hexane: dichloromethane, v:v, 3:1) to obtain 103 mg of red powder. The yield is 35%.
  • 82
  • [ 1714-27-8 ]
  • C27H28BrN3S [ No CAS ]
  • C43H37N3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 2-Bromopyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: C27H28BrN3S In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere; Schlenk technique; 6.2 (2) Synthesis of target molecule BTZ-DMAc-C6-PYR Add PYR-Br (140 mg, 0.5 mmol) to a 100 mL Schlenk flask, and add 20 mL of tetrahydrofuran that has been dewatered and deoxygenated under an argon atmosphere. Then, while stirring at -78 °C, 1.6 mol/L n-butyl lithium n-hexane solution (n-BuLi in hexane, 0.32 mL, 0.5 mmol) was slowly added dropwise to it. After the addition is complete, continue to stir at low temperature for 2 hours, BTZ-DMAc-C6-Br (253 mg, 0.5 mmol) was added thereto, followed by reaction at room temperature for 12 hours. The reaction was quenched with water, the reaction solution was poured into 50 mL ice water, extracted with dichloromethane three times, the organic phase was concentrated, and the column chromatography was separated (n-hexane: dichloromethane, v:v, 3:1) to obtain 125 mg of red powder. The yield is 40%.
  • 83
  • [ 1714-27-8 ]
  • C44H42(2)H7BO3 [ No CAS ]
  • C54H39(2)H7O [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.63% With palladium diacetate; potassium carbonate; XPhos In 1,4-dioxane; water at 90 - 105℃; for 8h; Inert atmosphere; 1 Synthesis of compound 5 Under the protection of inert gas, weigh 12.5g (0.09mol) potassium carbonate, 19.4g (0.030mol) intermediate a, 9.3g (0.033mol) 2-bromopyrene,0.070g (0.311mmol) palladium acetate, 0.370g (0.777mmol) 2-dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl in a 1L three-necked flask,Dissolve with 29.2g purified water and 388.0g dioxane, stir and raise the temperature to between 90.0-105.0°C, keep the temperature for 8.0h, HPLC: 95.9%.After extraction, washing with water, column chromatography, and toluene recrystallization, 16.8 g of light yellow solid compound 5 was obtained, with a total yield of 77.63%, HPLC: 99.9%
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