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[ CAS No. 863992-56-7 ] {[proInfo.proName]}

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Chemical Structure| 863992-56-7
Chemical Structure| 863992-56-7
Structure of 863992-56-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 863992-56-7 ]

CAS No. :863992-56-7 MDL No. :MFCD16294538
Formula : C26H32B2O4 Boiling Point : -
Linear Structure Formula :C14H8(BO2C2(CH3)4)2 InChI Key :ZLXSWNVYGSZXOP-UHFFFAOYSA-N
M.W : 430.15 Pubchem ID :57415691
Synonyms :

Calculated chemistry of [ 863992-56-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 32
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.46
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 134.41
TPSA : 36.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.39 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 6.39
Log Po/w (WLOGP) : 4.59
Log Po/w (MLOGP) : 2.86
Log Po/w (SILICOS-IT) : 3.91
Consensus Log Po/w : 3.55

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.72
Solubility : 0.0000811 mg/ml ; 0.000000189 mol/l
Class : Poorly soluble
Log S (Ali) : -6.96
Solubility : 0.0000474 mg/ml ; 0.00000011 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.84
Solubility : 0.00000062 mg/ml ; 0.0000000014 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.16

Safety of [ 863992-56-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P271-P261-P280 UN#:N/A
Hazard Statements:H319-H315-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 863992-56-7 ]

* 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 [ 863992-56-7 ]

[ 863992-56-7 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 523-27-3 ]
  • [ 73183-34-3 ]
  • [ 863992-56-7 ]
YieldReaction ConditionsOperation in experiment
85% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 24h;Inert atmosphere; Under an argon atmosphere, 9,10-dibromoanthracene (10g, 27.47mmol), bis-boronic acid ester (20.92g, 82.40mmol) and potassium acetate (13.48g, 137.33mmol), was added to 250 ml 1,4 - dioxane, was heated to 110 deg.] C, for 24 hours.The reaction mixture was poured into water and extracted with ethyl acetate, the organic layer was thoroughly washed with brine, dried over anhydrous magnesium sulfate was added.After the solution was concentrated to give crude product as a white solid, purified by silica gel column chromatography (eluent petroleum ether selecting / dichloromethane = 3/1, v / v ),the product stored in a refrigerator, to give a white solid, yield 85%.
71% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In 1,4-dioxane; at 95℃; for 24h; 9,10-dibromoanthracene (3.4 g, 0.010 mol) in bis (pinacolato) dibron (5.0 g, 0.024 mol), PdCl2 (dppf) (0.4 g, 0.0005 mol), potassium-acetate (2.7 g, 0.020 mol) into a 100 mL 1,4-dioxane and stirred for 24 hours at 95C . The reaction was then cooled to terminate the reaction H20: After layer separation the MC column purification (n-Hexane: MC) to the intermediate 14- 3.1 g (yield:71%) was obtained.
65.9% With sodium borate; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In N,N-dimethyl-formamide; at 80℃; for 24h;Inert atmosphere; In nitrogen atmosphere, a mixture with 3.36 g 9,10-dibromoanthracene, 5.6 g sodium borate, 6.0 g potassium acetate and 0.2 g Pd(dppf)Cl2 in 80 mL N,N-dimethylformamide was stirred at 80 C for 24 h. After cooling to room temperature, the reaction mixture was poured into icewater and rapidly stirred to precipitate crude product. The 9,10-bis(4' ,4' ,5' ,5? -tetramethyl-1' ,3' ,2? -borate) anthracene was obtained by column chromatography on silica gel with dichloromethane/petroleumether (1/5) as the eluant to obtain a faint yellow powder (yield 65.9%). 1H NMR (CDCl3, 400 MHz) delta 8.24 (d, J 3.6 Hz, 4H), 7.55 (dd, J 4.4,4.8 Hz, 4H), 1.58 (s, 24H); 13C NMR (CDCl3, 100 MHz) 25.41, 85.22,99.93, 126.35, 128.48, 134.45.
65% With tris-(dibenzylideneacetone)dipalladium(0); sodium acetate; In N,N-dimethyl-formamide;Inert atmosphere; Reflux; a, under the protection of nitrogen, 9,10-dibromoanthracene,Pinacol borate,Pd2 (dba) 3, sodium acetate was added to DMF,Heated to reflux overnight;After the reaction is cooled to room temperature,The combined organic phases were washed with water and extracted with ethyl acetate.Spin out the organic solvent and separate by column chromatographyTo give the compound 9,10-di-pinacol boronate,Is white powder,Yield 65%;
58% With potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 80℃; for 7h;Inert atmosphere; In a nitrogen atmosphere, 9,10-dibromoanthracene (6) (0.54 g, 1.61 mmol) and of bis(pinacolato)diboron (0.98 g, 3.86 mmol) were dissolved in DMF (20 mL), followed by the addition of palladium acetate (12 mg) and potassium acetate (0.473 g, 4.82 mmol). The reaction mixture was then stirred at 80 C for 7 h under nitrogen atmosphere. After that, the mixture was cooled to room temperature and poured into water (300 mL) with stirring. The solid was collected by filtration and dried. The crude product was purified by column chromatography (silica gel) with petroleum ether/dichloromethane (v/v = 1:1) as eluent, followed by recrystallized in petroleum ether/dichloromethane to give a green powder in a yield of 58 %. Mp>250 C. 1H NMR (500 MHz, TMS, CDCl3): delta (ppm) = 8.35-8.33 (m, 4H), 7.45-7.43 (m, 4H), 1.57 (s, 24H) (Fig. S12) IR (KBr, cm-1): 2980, 2930, 1720, 1450, 1240, 1140, 980, 852, 758, 675, 579. Elemental analysis calculated for C26H32B2O4: C, 72.60; H, 7.50. Found: C,72.51; H, 7.36. MS, m/z: cal: 430.2, found: 429.7 (Fig. S13)
36.3% With potassium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 70℃; for 18h;Inert atmosphere; Compound A (4.00 g, 11.91 mmol), bis (pinacolato) diboron (7.62 g, 30.00 mmol),Palladium (II) acetate (Palladium (II) acetate, Pd (OAc) 2) (0.15 g, 0.71 mmol), potassium acetate (Poassi acetate acetate, PoAc)(7.00 g, 71.4 mmol) and 35 mL of dimethylformamide (DMF) were placed in a flask, charged with nitrogen, and reacted at 70 C. for 18 hours.After cooling to room temperature, the product was extracted with methylene chloride (MC) and washed well with water. The extracted organics were dried over anhydrous magnesium sulfate (anhydrous MgSO 4). Then, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1 (eluent)) to obtain 1.86 g of compound A-1. (Yield 36.3%)
With potassium carbonate; palladium; In N,N-dimethyl-formamide; at 90 - 120℃;Inert atmosphere; In actual operation, under the protection of argon, 2 mmol-15 mmol of the first reactant 4 mmol-30 mmol of the second reactant 2 mmol- 41 mmol of potassium carbonate and 0.1 mmol-1.0 mmol of palladium catalyst, 20 mL-250 mL of dimethylformamide solvent was added thereto, and the mixture was heated and refluxed at 90 C-120 C for 48 hours-96 hours The mixture including the first intermediate product is cooled to room temperature at the end of the reaction, the solvent is distilled off under reduced pressure and distillation, and the product is extracted 3 to 5 times with deionized water and CH2Cl2. Extract 3 times to 5 times, dry the obtained organic phase with anhydrous sodium sulfate, then filter, spin-dry and chromatographically separate and purify to obtain the first intermediate product

  • 2
  • [ 863992-56-7 ]
  • [ 114648-37-2 ]
  • copolymer, Mn = 4300, Mw/Mn = 1.5, monomer(s): 9,10-bis(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)anthracene, 1,3-bis(4-bromophenyl)-1,3-diphenylallene [ No CAS ]
  • 3
  • [ 863992-56-7 ]
  • [ 774-53-8 ]
  • 9,10-bis(2,3'-bipyridine-5-yl)anthracene [ No CAS ]
  • 4
  • [ 863992-56-7 ]
  • [ 62913-27-3 ]
  • 9,10-bis(2,3'-bipyridine-6-yl)-2-phenylanthracene [ No CAS ]
  • 5
  • [ 863992-56-7 ]
  • [ 62913-27-3 ]
  • 9,10-bis(2,3'-bipyridin-6-yl)anthracene [ No CAS ]
  • 6
  • [ 863992-56-7 ]
  • [ 955959-05-4 ]
  • [ 955958-99-3 ]
  • 7
  • [ 863992-56-7 ]
  • [ 955959-04-3 ]
  • [ 955959-05-4 ]
  • [ 1112955-48-2 ]
  • 8
  • [ 863992-56-7 ]
  • [ 955959-04-3 ]
  • [ 955959-03-2 ]
  • 10
  • [ 863992-56-7 ]
  • [ 1258422-45-5 ]
  • [ 1258422-44-4 ]
  • 11
  • [ 863992-56-7 ]
  • [ 1258605-42-3 ]
  • 12
  • [ 863992-56-7 ]
  • [ 1384861-56-6 ]
  • 13
  • [ 863992-56-7 ]
  • 9,10-bis(biphenyl-3-yl)anthracene [ No CAS ]
  • 14
  • [ 863992-56-7 ]
  • [ 625-92-3 ]
  • 9,10-bis[5-bromopyrid-3-yl]anthracene [ No CAS ]
  • 15
  • [ 863992-56-7 ]
  • [ 108-36-1 ]
  • [ 872965-18-9 ]
  • 16
  • [ 61676-62-8 ]
  • [ 523-27-3 ]
  • [ 863992-56-7 ]
YieldReaction ConditionsOperation in experiment
76% Under an argon atmosphere, 9,10-dibromoanthracene (336 mg, 1.0 mmol) was dissolved in THF (5 mL)It was cooled to -78 C. To this was added a hexane solution of butyllithium (2.78 M, 0.79 mL, 2.2 mmol). The mixture was stirred at the same temperature for 2 hours and then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaboralone (0.60 mL, 3.0 mmol) was added.The reaction solution was warmed to room temperature and stirred for 15 hours, and then saturated aqueous ammonium chloride solution (5 mL) and chloroform (5 mL) were added. After separating the organic layer, the aqueous layer was extracted twice with chloroform and the organic layer was dried with sodium sulfate. After removing the drying agent by filtration, the low boiling point fraction was removed under reduced pressure from the filtrate to obtain a crude product. The crude product was purified by silica gel chromatography (hexane / chloroform = 80: 20 to 0: 100) to give 9,10-bis (4,4,5,5-tetramethyl-1,3-dioxaborolane- Yl) anthracene as a white solid (327 mg, 0.76 mmol, 76%).
  • 17
  • [ 863992-56-7 ]
  • [ 624-38-4 ]
  • [ 452069-70-4 ]
  • 18
  • [ 863992-56-7 ]
  • [ 628336-83-4 ]
  • [ 1417805-85-6 ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In toluene; at 85℃; for 48h;Inert atmosphere; General procedure: A mixture of 3-bromo-9-octyl-9H-carbazole (1) (2.0 g, 5.59 mmol), <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (7) (1.0 g, 2.33 mmol), degassed toluene (30 mL) and degassed aqueous K2CO3 solution (25 mL, 2 M) was stirred at 85 C for 48 h under N2 atmosphere, and was then cooled to room temperature. The resulting green solution was extracted with CH2Cl2 (3 × 30 mL). The organic phase was combined, washed with brine and then dried with anhydrous MgSO4. After the solvent was removed, the crude product was purified by column chromatography (silica gel) with petroleum ether/dichloromethane (v/v = 10/1) as eluent, followed by recrystallized in THF/ethanol to give a yellow-green solid (1.13 g, 66 %). 1H NMR (500 MHz, TMS, CDCl3): delta (ppm) = 8.24 (s, 2H), 8.08 (t, J = 6.5 Hz, 2H), 7.83-7.81 (m, 4H), 7.64 (dd, J = 2.0 Hz, J = 8.5 Hz, 2H), 7.60 (d, J = 8.5 Hz, 2H), 7.52-7.49 (m, 4H), 7.31-7.29 (m, 4H), 7.24-7.22 (m, 2H), 4.44 (t, J = 7.0 Hz, 4H), 2.05-1.99 (m, 4H), 1.45-1.24 (m, 20H), 0.90 (t, J = 6.5 Hz, 6H) (Fig. S14) 13C NMR (125 MHz, CDCl3) delta (ppm) = 140.96, 139.89, 137.84, 130.73, 129.41, 129.06, 129.03, 125.87, 124.80, 123.25, 123.21, 122.96, 122.94, 122.77, 120.54, 120.52, 118.96, 108.88, 108.56, 108.53, 43.41, 31.86, 29.72, 29.47, 29.27, 29.18, 27.48, 22.67, 14.13 (Fig. S15). IR (KBr, cm-1): 2930, 2850, 1650, 1490, 1470, 1380, 1150, 1120, 804, 748. Elemental analysis calculated for C54H56N2: C, 88.48; H, 7.70; N, 3.82. Found: C, 88.43; H, 7.69; N, 3.88. MS, m/z: cal: 733.0, found: 732.2 (Fig. S16). Mp > 250.0 C.
  • 19
  • [ 863992-56-7 ]
  • [ 628337-00-8 ]
  • [ 1417805-84-5 ]
YieldReaction ConditionsOperation in experiment
66% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In toluene; at 85℃; for 48h;Inert atmosphere; General procedure: A mixture of 3-bromo-9-octyl-9H-carbazole (1) (2.0 g, 5.59 mmol), <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (7) (1.0 g, 2.33 mmol), degassed toluene (30 mL) and degassed aqueous K2CO3 solution (25 mL, 2 M) was stirred at 85 C for 48 h under N2 atmosphere, and was then cooled to room temperature. The resulting green solution was extracted with CH2Cl2 (3 × 30 mL). The organic phase was combined, washed with brine and then dried with anhydrous MgSO4. After the solvent was removed, the crude product was purified by column chromatography (silica gel) with petroleum ether/dichloromethane (v/v = 10/1) as eluent, followed by recrystallized in THF/ethanol to give a yellow-green solid (1.13 g, 66 %). 1H NMR (500 MHz, TMS, CDCl3): delta (ppm) = 8.24 (s, 2H), 8.08 (t, J = 6.5 Hz, 2H), 7.83-7.81 (m, 4H), 7.64 (dd, J = 2.0 Hz, J = 8.5 Hz, 2H), 7.60 (d, J = 8.5 Hz, 2H), 7.52-7.49 (m, 4H), 7.31-7.29 (m, 4H), 7.24-7.22 (m, 2H), 4.44 (t, J = 7.0 Hz, 4H), 2.05-1.99 (m, 4H), 1.45-1.24 (m, 20H), 0.90 (t, J = 6.5 Hz, 6H) (Fig. S14) 13C NMR (125 MHz, CDCl3) delta (ppm) = 140.96, 139.89, 137.84, 130.73, 129.41, 129.06, 129.03, 125.87, 124.80, 123.25, 123.21, 122.96, 122.94, 122.77, 120.54, 120.52, 118.96, 108.88, 108.56, 108.53, 43.41, 31.86, 29.72, 29.47, 29.27, 29.18, 27.48, 22.67, 14.13 (Fig. S15). IR (KBr, cm-1): 2930, 2850, 1650, 1490, 1470, 1380, 1150, 1120, 804, 748. Elemental analysis calculated for C54H56N2: C, 88.48; H, 7.70; N, 3.82. Found: C, 88.43; H, 7.69; N, 3.88. MS, m/z: cal: 733.0, found: 732.2 (Fig. S16). Mp > 250.0 C.
  • 20
  • [ 863992-56-7 ]
  • [ 1343990-86-2 ]
  • [ 1417805-86-7 ]
YieldReaction ConditionsOperation in experiment
46% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In toluene; at 85℃; for 48h;Inert atmosphere; General procedure: A mixture of 3-bromo-9-octyl-9H-carbazole (1) (2.0 g, 5.59 mmol), <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (7) (1.0 g, 2.33 mmol), degassed toluene (30 mL) and degassed aqueous K2CO3 solution (25 mL, 2 M) was stirred at 85 C for 48 h under N2 atmosphere, and was then cooled to room temperature. The resulting green solution was extracted with CH2Cl2 (3 × 30 mL). The organic phase was combined, washed with brine and then dried with anhydrous MgSO4. After the solvent was removed, the crude product was purified by column chromatography (silica gel) with petroleum ether/dichloromethane (v/v = 10/1) as eluent, followed by recrystallized in THF/ethanol to give a yellow-green solid (1.13 g, 66 %). 1H NMR (500 MHz, TMS, CDCl3): delta (ppm) = 8.24 (s, 2H), 8.08 (t, J = 6.5 Hz, 2H), 7.83-7.81 (m, 4H), 7.64 (dd, J = 2.0 Hz, J = 8.5 Hz, 2H), 7.60 (d, J = 8.5 Hz, 2H), 7.52-7.49 (m, 4H), 7.31-7.29 (m, 4H), 7.24-7.22 (m, 2H), 4.44 (t, J = 7.0 Hz, 4H), 2.05-1.99 (m, 4H), 1.45-1.24 (m, 20H), 0.90 (t, J = 6.5 Hz, 6H) (Fig. S14) 13C NMR (125 MHz, CDCl3) delta (ppm) = 140.96, 139.89, 137.84, 130.73, 129.41, 129.06, 129.03, 125.87, 124.80, 123.25, 123.21, 122.96, 122.94, 122.77, 120.54, 120.52, 118.96, 108.88, 108.56, 108.53, 43.41, 31.86, 29.72, 29.47, 29.27, 29.18, 27.48, 22.67, 14.13 (Fig. S15). IR (KBr, cm-1): 2930, 2850, 1650, 1490, 1470, 1380, 1150, 1120, 804, 748. Elemental analysis calculated for C54H56N2: C, 88.48; H, 7.70; N, 3.82. Found: C, 88.43; H, 7.69; N, 3.88. MS, m/z: cal: 733.0, found: 732.2 (Fig. S16). Mp > 250.0 C.
  • 21
  • [ 120-12-7 ]
  • [ 863992-56-7 ]
  • 22
  • [ 863992-56-7 ]
  • [ 98420-98-5 ]
  • [ 1257879-36-9 ]
  • 23
  • [ 76-09-5 ]
  • [ 251659-87-7 ]
  • [ 863992-56-7 ]
  • 24
  • [ 863992-56-7 ]
  • [ 29176-55-4 ]
  • C52H46B2N2O4 [ No CAS ]
  • 26
  • [ 76347-13-2 ]
  • [ 863992-56-7 ]
  • 27
  • 2-(10-bromoanthracene-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 76347-13-2 ]
  • [ 863992-56-7 ]
  • 28
  • [ 523-27-3 ]
  • [ 76347-13-2 ]
  • [ 863992-56-7 ]
  • 29
  • [ 863992-56-7 ]
  • C26H32B2MgO4 [ No CAS ]
  • 30
  • [ 863992-56-7 ]
  • C30H37BrN2O2 [ No CAS ]
  • C74H82N4O4 [ No CAS ]
  • 31
  • [ 850650-61-2 ]
  • [ 863992-56-7 ]
  • C36H31BO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 65℃; Intermediate 1-3 (3.5 g, 0.010 mol) in phenyl-boronic-acid (1.4 g, 0.012 mol), Pd (pph3) 4 (0.6 g, 0.0005 mol), potassium carbonate (2.8 g, 0.020 mol) in THF 100 put mL was reacted by stirring at 65C for 18 hours. After the reaction cooled to H20: After layer separation the MC column purification (N-HEXANE: MC) to give 2.0 g (51% yield). Intermediate 14-3 (3.5 g, 0.010 mol), intermediate 14-4 (5.2 g, 0.012 mol) were placed in Example 8-Preparation Example 1 in the same manner as in synthesis <intermediate 14-5> 3.2 g (yield: to give a 64%).
  • 32
  • [ 863992-56-7 ]
  • C36H23Br [ No CAS ]
  • 33
  • [ 863992-56-7 ]
  • C17H9F3O4S [ No CAS ]
  • C46H26O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 65℃; for 17h; 3.43 g of Intermediate 1-4 and 3.18 g of <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> were diluted with 100 ml of THF and 50 mP of water, 860 mg of Pd(PPh3)4and 0.2 g of potassium carbonate were added thereto, and then, at a temperature of 65 C., the mixture was refluxed for 17 hours. The result was extracted three times by using ethyl acetate, and an organic layer was dried by using anhydrous magnesium sulfate, and concentrated under reduced pressure and the residual was purified by silica gel column chromatography to obtain Compound 1 (5 g, 92%).
  • 34
  • [ 863992-56-7 ]
  • [ 79387-71-6 ]
  • 5,5'-(anthracene-9,10-diyl)bis(thiophene-5,2-diyl)dimethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 90℃; for 2h; A solution of (5-bromothien-2-yl)methanol (2) (100 mg, 0.52 mmole, 2.09 eq) and Pd(PPh3)4 (30 mg, 0.026 mmole, 0.05 eq) in 2 ml of 1,4-dioxane was stirred for several minutes, at room temperature. A mixture containing 107 mg (0.25 mmole, 1eq) of <strong>[863992-56-7]anthracene-9,10-diboronic acid bis(pinacol) ester</strong> (3) and K2CO3 (51.8 mg, 0.375 mmole, 1.5 eq) in 1,4-dioxane-H2O (2:1) was added to the solution above, then was refluxed at 90 C for 2hr. After checking by TLC (EA:Hx = 1:1, Rf = 0.25), the reaction was stopped and then separated by silica gel chromatography (EA:Hx = 1 : 5) to give 62.3 mg (62% yield) of an yellow solid (TA).
  • 35
  • [ 863992-56-7 ]
  • [ 1309387-42-5 ]
  • C106H114N4O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate; In N,N-dimethyl-formamide; toluene; at 100℃;Inert atmosphere; PBDT-FTTE (PTB7) was purchased from Solarmer Inc. 9,10-Anthracenediboronic acid bis(pinacol) ester (M1) was purchasedfrom Sigma-Aldrich. 5-bromo-2,9-di(undecan-6-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone (M2)were synthesized as reported elsewhere [29]. In order to synthesizeAn(PDI)2, a 50 ml round-bottom flask, a mixture of M1 (430.2 mg,1 mmol) and M2 (1788.9 mg, 2.3 mmol) was dissolved in themixture of degassed toluene and DMF (20 ml, 4:1 in volume ratio)The aqueous solution of K2CO3 (2 M, 15 ml) was added in the solutionunder N2 atmosphere. After the solution was furtherdegassed for 10 min, the mixturewas stirred at 100 C for overnightand then the solution was cooled down to room temperature. Toquench the coupling reaction, the mixturewas poured into 50ml ofMeOH/H2O (1:1 in vol) After the mixture was extracted withmethylene chloride, the organic phase was dried over MgSO4. Thecrude product was further purified by flash chromatography usinghexane:methylenechloride (2:1) mixture to yield a dark purplesolid (880 mg, Y = 60%). 1H NMR (300 Hz, CDCl3): 8.75-8.58 (1,8 m), 8.45-8.30 (m, 4H), 8.20-7.75 (d, 6H), 7.30 (d, 2H), 7.15 (d, 4H),3.62 (m, 4H), 1.89 (m, 12H), 1.45-1.20 (m, 4H), 0.88-0.84 (m, 70H).HRMS Calculated for C106H114N4O8 1572.10 found: m/z 1571.88,Anal. Cal. for C106H114N4O8 C, 80.99; H, 7.31; N, 3.56, Found: C,80.92; H, 7.30; N, 3.66.
  • 37
  • [ 863992-56-7 ]
  • [ 1271080-05-7 ]
  • C58H70O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69 mg With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In N,N-dimethyl-formamide; at 20 - 50℃; for 24h;Inert atmosphere; To a round-bottomed flask, 9,10-anthracenediboronic acid bispinacol ester (Aldrich, 430 mg, 1 mmol),Compound 11-1 (750 mg, 2.1 mmol), potassium phosphate (1.27 g, 6 mmol),Tris (dibenzylideneacetone) dipalladium (hereinafter referred to as Pd 2 (dba) 3) (18.2 mg),Tri-tert-butylphosphine (9.7 mg) was added,After replacing with argon gas, DMF (25 mL) was added,And the mixture was stirred at room temperature for 24 hours. Saturated ammonium chloride aqueous solution was added,After stirring for 30 minutes, ethyl acetate was added to separate the organic layer,The aqueous layer was extracted four times with ethyl acetate.The combined organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, followed by water and saturated brine, and dried over magnesium sulfate. The desiccant was filtered off.The concentrated residue thin-layer chromatography (developing solvent: toluene) was analyzed, the two products was confirmed.The two components were separated and purified with a silica gel column (developing solvent: toluene)HTL 1 was obtained as a main product as a pale yellow solid.HTL 1 (yield 69 mg) Compound 4 was used instead of compound 11-1 in Example 1,In the same manner except that the reaction temperature was changed from room temperature to 50 C.,
  • 38
  • [ 863992-56-7 ]
  • C22H31IO4 [ No CAS ]
  • C58H70O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In N,N-dimethyl-formamide; at 20 - 50℃;Inert atmosphere; General procedure: To a round-bottomed flask, 9,10-anthracenediboronic acid bispinacol ester (Aldrich, 430 mg, 1 mmol),Compound 11-1 (750 mg, 2.1 mmol), potassium phosphate (1.27 g, 6 mmol),Tris (dibenzylideneacetone) dipalladium (hereinafter referred to as Pd 2 (dba) 3) (18.2 mg),Tri-tert-butylphosphine (9.7 mg) was added,After replacing with argon gas, DMF (25 mL) was added,And the mixture was stirred at room temperature for 24 hours. Saturated ammonium chloride aqueous solution was added,After stirring for 30 minutes, ethyl acetate was added to separate the organic layer,The aqueous layer was extracted four times with ethyl acetate.The combined organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, followed by water and saturated brine, and dried over magnesium sulfate. The desiccant was filtered off.The concentrated residue thin-layer chromatography (developing solvent: toluene) was analyzed, the two products was confirmed.The two components were separated and purified with a silica gel column (developing solvent: toluene)HTL 1 was obtained as a main product as a pale yellow solid.HTL 1 (yield 69 mg) In the same manner as in Example 1 except that the compound 5 was used in place of the compound 11-1, the reaction time was changed from 24 hours to 48 hours, and the reaction temperature was changed from room temperature to 50 C., the synthesis of HTL4 and Purification was performed. As a pale yellow waxy solid, HTL 4 was obtained. (Yield 53 mg, Yield 33%)
  • 39
  • [ 863992-56-7 ]
  • [ 1352790-35-2 ]
  • C46H46O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
69 mg With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere; To a round-bottomed flask, 9,10-anthracenediboronic acid bispinacol ester (Aldrich, 430 mg, 1 mmol),Compound 11-1 (750 mg, 2.1 mmol), potassium phosphate (1.27 g, 6 mmol),Tris (dibenzylideneacetone) dipalladium (hereinafter referred to as Pd 2 (dba) 3) (18.2 mg),Tri-tert-butylphosphine (9.7 mg) was added,After replacing with argon gas, DMF (25 mL) was added,And the mixture was stirred at room temperature for 24 hours. Saturated ammonium chloride aqueous solution was added,After stirring for 30 minutes, ethyl acetate was added to separate the organic layer,The aqueous layer was extracted four times with ethyl acetate.The combined organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution, followed by water and saturated brine, and dried over magnesium sulfate. The desiccant was filtered off.The concentrated residue thin-layer chromatography (developing solvent: toluene) was analyzed, the two products was confirmed.The two components were separated and purified with a silica gel column (developing solvent: toluene)HTL 1 was obtained as a main product as a pale yellow solid.HTL 1 (yield 69 mg)
  • 40
  • [ 863992-56-7 ]
  • [ 135484-83-2 ]
  • dimethyl 4,4'-(9,10-anthracenediyl)bis(2-aminobenzoate) [ No CAS ]
  • 41
  • [ 863992-56-7 ]
  • [ 1122-91-4 ]
  • [ 324750-99-4 ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 78℃;Inert atmosphere; General procedure: The optimized procedure is based on similar reports.S8,S9 To a solution of <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (1) (0.930 mmol), brominated aromatic aldehyde (2.800 mmol) and Pd(PPh3)4 ( 0.140 mmol) in THF (30 mL), was added drop-wise an aqueous solution of K2CO3 (2.6 mL, 2M) at room temperature under argon atmosphere. After refluxing at 78 C for 12 hours, the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid residue was dissolved in DCM and washed with water. The organic layers were dried over MgSO4 and concentrated. Further purification was carried out by silica column chromatography.
  • 42
  • [ 863992-56-7 ]
  • [ 1122-91-4 ]
  • C34H18N4 [ No CAS ]
  • 43
  • [ 863992-56-7 ]
  • [ 4701-17-1 ]
  • 5,5'-(anthracene-9,10-diyl)bis(thiophene-2-carbaldehyde) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 78℃;Inert atmosphere; General procedure: The optimized procedure is based on similar reports.S8,S9 To a solution of <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (1) (0.930 mmol), brominated aromatic aldehyde (2.800 mmol) and Pd(PPh3)4 ( 0.140 mmol) in THF (30 mL), was added drop-wise an aqueous solution of K2CO3 (2.6 mL, 2M) at room temperature under argon atmosphere. After refluxing at 78 C for 12 hours, the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid residue was dissolved in DCM and washed with water. The organic layers were dried over MgSO4 and concentrated. Further purification was carried out by silica column chromatography.
  • 44
  • [ 863992-56-7 ]
  • [ 4701-17-1 ]
  • C30H14N4S2 [ No CAS ]
  • 45
  • [ 863992-56-7 ]
  • [ 110046-60-1 ]
  • C32H18O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 78℃;Inert atmosphere; General procedure: The optimized procedure is based on similar reports.S8,S9 To a solution of <strong>[863992-56-7]9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene</strong> (1) (0.930 mmol), brominated aromatic aldehyde (2.800 mmol) and Pd(PPh3)4 ( 0.140 mmol) in THF (30 mL), was added drop-wise an aqueous solution of K2CO3 (2.6 mL, 2M) at room temperature under argon atmosphere. After refluxing at 78 C for 12 hours, the reaction mixture was cooled to room temperature. The solvent was evaporated under reduced pressure. The solid residue was dissolved in DCM and washed with water. The organic layers were dried over MgSO4 and concentrated. Further purification was carried out by silica column chromatography.
  • 46
  • [ 863992-56-7 ]
  • [ 610-94-6 ]
  • 9,10-bis(methyl-2-benzoate)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In toluene; at 110℃; for 16h;Inert atmosphere; Under an argon atmosphere, 9,10-dibromoanthracene boronic ester (10g, 21.82mmol), sodium carbonate (11.57g, 109.12mmol) and 2-bromobenzoic acid methyl ester(14.08g, 65.47mmol) was added 250 ml toluene was completely dissolved, then add tetrakis (triphenylphosphine) palladium (504.39mg, 436.49umol), heated to 110 deg.] C, for 16 hours.The reaction mixture was poured into water and extracted with ethyl acetate, the organic layer was thoroughly washed with brine, dried over anhydrous magnesium sulfate was added.After the solution was concentrated to give crude product as a white solid, purified by silica gel column chromatography (eluent petroleum ether selecting / dichloromethane = 3/1, v / v ),the product stored in a refrigerator, to give a white solid, yield 85%.
  • 47
  • [ 605-48-1 ]
  • [ 73183-34-3 ]
  • [ 863992-56-7 ]
  • 48
  • [ 863992-56-7 ]
  • [ 5315-25-3 ]
  • 9,10-bis(6-methylpyrid-2-yl)anthracene [ No CAS ]
  • 49
  • [ 863992-56-7 ]
  • C50H38B2N2 [ No CAS ]
  • 51
  • [ 863992-56-7 ]
  • [ 5737-94-0 ]
  • 52
  • [ 863992-56-7 ]
  • 8,16-bis((triisopropylsilyl)ethynyl)dibenzo[a,j]perylene [ No CAS ]
  • 53
  • [ 863992-56-7 ]
  • 2,4-bis(4-(tert-butyl)phenyl)-6-chloro-1,3,5-triazine [ No CAS ]
  • 9,10-bis[4,6-bis(4-tert-butylphenyl)-1,3,5-triazin-2-yl]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0); In toluene; at 115℃; for 24h;Inert atmosphere; Under an argon atmosphere, 4,6-bis (4-tert-butylphenyl) -2-chloro-1,3,5-triazine (232 mg, 0.6 mmol) synthesized in Reference Example 3,9,10-bis (4,4,5,5-tetramethyl-1,3-dioxyboran-2-yl) anthracene (86 mg, 0,2 mol) synthesized in Reference Example 1,Tetrakis (triphenylphosphine) palladium (23 mg, 20 mumol)And potassium phosphate (255 mg, 1.2 mmol) were dissolved in toluene (2 mL). The mixture was stirred at 115 C. for 24 hours, then allowed to cool to room temperature, and water (5 mL) and chloroform (5 mL) were added. After separating the organic layer, the aqueous layer was extracted twice more and the organic layer was dried over sodium sulfate. After removing the drying agent by filtration, the low boiling point fraction was removed under reduced pressure from the filtrate to obtain a crude product. The crude product was purified by silica gel chromatography (hexane / chloroform = 80: 20 to 50: 50)9,10-bis [4,6-bis (4-tert-butylphenyl) -1,3,5-triazin-2-yl] anthracene was obtained as a white solid (142 mg, 33 mumol, 82%).
  • 54
  • [ 863992-56-7 ]
  • [ 21902-35-2 ]
  • 9,10-bis[4,6-bis(4-methoxyphenyl)-1,3,5-triazin-2-yl]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 105℃; for 48h; Under an argon atmosphere, 2-chloro-4,6-bis (4-methoxyphenyl) -1,3,5-triazine (197 mg, 0.6 mmol) synthesized in Reference Example-8,9,10-bis (4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl) anthracene (86 mg, 0.2 mmol) synthesized in Reference Example 1 and tetrakis (triphenylphosphine) Palladium (46 mg, 40 mumol) was added dioxane (2 mL) and 2 M aqueous potassium phosphate solution (0.6 mL, 1.2 mmol). This mixed solution was stirred at 105 C. for 48 hours, then allowed to cool to room temperature, and water and methanol were added. The resulting solid was washed with water and methanol to obtain a crude product. The crude product was purified by Soxhlet extraction (chloroform) to obtain 9,10-bis [4,6-bis (4-methoxyphenyl) -1,3,5-triazin-2-yl] anthracene as a pale yellow solid Obtained (115 mg, 0.15 mmol, 76%)
  • 55
  • [ 863992-56-7 ]
  • 2-chloro-4,6-bis[4-(2,2-dimethylpropyloxy)phenyl]-1,3,5-triazine [ No CAS ]
  • 9,10-bis{4,6-bis[4-(2,2-dimethylpropyloxy)phenyl]-1,3,5-triazin-2-yl}anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 105℃; for 22h;Inert atmosphere; Under an argon atmosphere,2-chloro-4,6-bis [4- (2,2-dimethylpropyloxy) phenyl] -1,3,5-triazine (53 mg, 0.12 mmol) synthesized in Reference Example-9,9,10-bis (4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl) anthracene (17 mg, 40 mumol) synthesized in Reference Example 1 and tetrakis (triphenylphosphine) palladium 9 mg, 8 mumol), dioxane (0.8 mL) and 2 M aqueous potassium phosphate solution (120 muL, 0.24 mmol) were added. The mixed solution was stirred at 105 C. for 22 hours, then allowed to cool to room temperature, and water and methanol were added. The resulting solid was washed with water and methanol to obtain a crude product. The crude product was purified by silica gel chromatography (hexane / chloroform = 95: 5 to 0: 100) to obtain 9,10-bis {4,6-bis [4- (2,2-dimethylpropyloxy) phenyl] -1,3,5-triazin-2-yl} anthracene as a pale yellow solid (32 mg, 33 mumol, 82%).
  • 56
  • [ 863992-56-7 ]
  • 2-chloro-4,6-bis[4-(2,2-dimethylpropylsulfanyl)phenyl]-1,3,5-triazine [ No CAS ]
  • 9,10-bis{4,6-bis[4-(2,2-dimethylpropylsulfanyl)phenyl]-1,3,5-triazin-2-yl}anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; at 105℃; for 22h;Inert atmosphere; Under argon atmosphere, 2-chloro-4,6-bis [4- (2,2-dimethylpropylsulfanyl) phenyl] -1,3,5-triazine (283 mg, 0.60 mmol) synthesized in Reference Example- , 9,10-bis (4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl) anthracene (86 mg, 20 mmol) synthesized in Reference Example 1 and tetrakis (triphenylphosphine) palladium (46 mg, 40 mumol), dioxane (2 mL) and 2 M aqueous potassium phosphate solution (0.6 mL, 1.2 mmol) were added. The mixed solution was stirred at 105 C. for 22 hours, then allowed to cool to room temperature, and water and methanol were added. The resulting solid was washed with water and methanol to obtain a crude product. The crude product was purified by silica gel chromatography (hexane / chloroform = 80: 20 to 0: 100) to obtain 9,10-bis {4,6-bis [4- (2,2- dimethylpropylsulfanyl) phenyl] -1,3,5-triazin-2-yl} anthracene as a pale yellow solid (177 mg, 0.17 mmol, 84%).
  • 57
  • [ 863992-56-7 ]
  • [ 69243-19-2 ]
  • C40H46O8 [ No CAS ]
  • 58
  • [ 863992-56-7 ]
  • [ 3430-17-9 ]
  • 9,10-bis(5-methylpyrid-2-yl)anthracene [ No CAS ]
  • 59
  • [ 863992-56-7 ]
  • C34H38B2N2O2 [ No CAS ]
  • 60
  • [ 863992-56-7 ]
  • [ 3510-66-5 ]
  • C34H38B2N2 [ No CAS ]
  • 61
  • [ 863992-56-7 ]
  • [ 3510-66-5 ]
  • 9,10-bis(3-methylpyrid-2-yl)anthracene [ No CAS ]
  • 62
  • [ 863992-56-7 ]
  • [ 4926-28-7 ]
  • 9,10-bis(4-methylpyrid-2-yl)anthracene [ No CAS ]
  • 63
  • [ 863992-56-7 ]
  • 10-(4-bromophenyl)-9-phenyl-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 9,10-bis(4-(9-phenyl-9H-pyreno[4,5-d]imidazole)-10-phenyl)-anthracene [ No CAS ]
  • 64
  • [ 863992-56-7 ]
  • 9-(4-bromophenyl)-10-phenyl-9H-pyreno[4,5-d]imidazole [ No CAS ]
  • 9,10-bis(4-(10-phenyl-9H-pyreno[4,5-d]imidazole)-9-phenyl)-anthracene [ No CAS ]
  • 65
  • [ 863992-56-7 ]
  • C69H73BrOS4 [ No CAS ]
  • C152H154O2S8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.9% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 70℃; for 24h;Inert atmosphere; Compound A-1 (0.28 g, 0.67 mmol), Compound B-1 (1.70 g, 1.51 mmol), tetrakis (triphenylphosphine) palladium (0) (Pd (PPh3) 4) (0.031 g, 0.27 mmol) , 2 M potassium carbonate (K2CO3) (4 mL, 8 mmol)And tetrahydrofuran (THF) (16 mL) into the flask,Charged with nitrogen and reacted at 70 C. for 24 hours.After cooling to room temperature, the product was extracted with methylene chloride (MC) and washed well with water. The extracted organics were dried over anhydrous magnesium sulfate (anhydrous MgSO 4).Then silica gel column chromatography (hexane: dichloromethane = 1: 1(Eluent)) to give 1.2 g of compound 1-1. (Yield 78.9%)
  • 66
  • [ 863992-56-7 ]
  • C61H65BrOS8 [ No CAS ]
  • C136H138O2S16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.5% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 70℃; for 24h;Inert atmosphere; Compound A-1 (0.28 g, 0.67 mmol), compound C-1 (1.74 g, 1.51 mmol), Pd (pph3) 4 (0.031 g, 0.27 mmol),2M K2CO3 (4 mL, 8 mmol) and THF (16 mL) were placed in the flask,Charged with nitrogen and reacted at 70 C. for 24 hours.After cooling to room temperature, the product was extracted with methylene chloride (MC) and washed well with water. The extracted organics were dried over anhydrous magnesium sulfate (anhydrous MgSO 4). Then silica gel column chromatography(Hexane: dichloromethane = 1: 1 (eluent))Purified with 0.94 g of compound 5-1. (Yield 60.5%)
  • 67
  • [ 863992-56-7 ]
  • [ 1361418-07-6 ]
  • C144H154O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.8% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 70℃; for 24h;Inert atmosphere; Compound A-1(0.28 g, 0.67 mmol), compound D-1 (1.53 g, 1.51 mmol),Pd (pph3) 4 (0.031 g, 0.27 mmol), 2M Put K2CO3 (4 mL, 8 mmol) and THF (16 mL) into the flask,Charged with nitrogen and reacted at 70 C. for 24 hours. After cooling to room temperature, the product was extracted with methylene chloride (MC) and washed well with water.The extracted organics were dried over anhydrous magnesium sulfate (anhydrous MgSO 4). Then silica gel column chromatographyCompound purified by (hexane: dichloromethane = 1: 1 (eluent))0.97g of 9-1 were obtained. (Yield 70.8%)
  • 68
  • [ 863992-56-7 ]
  • [ 22532-62-3 ]
  • C28H18O4 [ No CAS ]
  • 69
  • [ 863992-56-7 ]
  • [ 67-56-1 ]
  • C18H20B2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% b. Under the protection of nitrogen, 9,10-di-pinalcol anthracene was added to the acetic acid solution of ammonium acetate.Stir for 5h, add sodium bicarbonate to neutralize, extract with ethyl acetate, dry over magnesium sulfate,The solvent was concentrated under reduced pressure, then dissolved in methanol and refluxed overnight.Spin-dry the solvent,To give 9,10-bis (dimethoxy) boranthracene,Yield 95%;
  • 70
  • [ 863992-56-7 ]
  • C19H20BrNO2 [ No CAS ]
  • C52H48N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium; bis(pinacol)diborane; In water; toluene; at 90 - 100℃;Inert atmosphere; In actual operation, under the protection of argon, 1 mmol-10 mmol of the first intermediate product 1 mmol-10 mmol of dioxaborolane and 0.1 mmol are added to the reaction vessel molar-5 mmol of palladium catalyst, The second intermediate product dissolved in toluene is then added to the reaction vessel, Add 1-100 ml of deionized water and react at 90 C-100 C for 36 hours-58 hours to obtain a mixture including the electroluminescent material. After cooling to room temperature after the end of the reaction, the solvent was distilled off under reduced pressure and distillation. The product was extracted with deionized water and CH2Cl2 3 times-5 times. After the organic phase was separated, it was back extracted with deionized water 3 times-5 times. Dry the obtained organic phase with anhydrous sodium sulfate, then filter, spin-dry and chromatographically separate and purify to obtain the electroluminescent material:
  • 71
  • [ 863992-56-7 ]
  • [ 2685737-72-6 ]
  • [ 2685737-74-8 ]
YieldReaction ConditionsOperation in experiment
34% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 85℃; for 24h; Inert atmosphere;
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water Inert atmosphere;
  • 72
  • [ 863992-56-7 ]
  • [ 38170-02-4 ]
  • [ 2412193-73-6 ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 48h; Inert atmosphere; Schlenk technique; Darkness;
  • 73
  • [ 863992-56-7 ]
  • [ 589-87-7 ]
  • [ 24672-72-8 ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In tetrahydrofuran; lithium hydroxide monohydrate for 36h; Reflux; Inert atmosphere;
  • 74
  • [ 863992-56-7 ]
  • [ 67665-47-8 ]
  • [ 2756158-98-0 ]
YieldReaction ConditionsOperation in experiment
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran at 80℃; for 12h; 5 (5) intermediate (e) Referring to the above reaction formula,In a 500mL two-neck flask under nitrogen atmosphere, 2,2'-dibromo-9,9'-spirobi[fluorene](0.5g, 2mmol), 9,10-bis(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)anthracene (0.6g, 2mmol),Pd(pph3)4 (0.2g, 0.0002mol) was added,Add THF (100 mL) and stir. When all the substances are dissolved in the flask, add potassium carbonzte solution (2N, 100mL). The reaction proceeds by refluxing at 80° C. for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate/distilled water to separate the organic layer. After all of the solvent of the separated organic layer is blown off, it is purified by column chromatography (methylene chloride: hexane = 1:4) to obtain the following intermediate (e).
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran at 80℃; for 12h; 5 (5) intermediate (e) Referring to the above reaction formula,In a 500mL two-neck flask under nitrogen atmosphere, 2,2'-dibromo-9,9'-spirobi[fluorene](0.5g, 2mmol), 9,10-bis(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)anthracene (0.6g, 2mmol),Pd(pph3)4 (0.2g, 0.0002mol) was added,Add THF (100 mL) and stir. When all the substances are dissolved in the flask, add potassium carbonzte solution (2N, 100mL). The reaction proceeds by refluxing at 80° C. for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate/distilled water to separate the organic layer. After all of the solvent of the separated organic layer is blown off, it is purified by column chromatography (methylene chloride: hexane = 1:4) to obtain the following intermediate (e).
  • 75
  • [ 863992-56-7 ]
  • [ 2245080-07-1 ]
  • [ 2254808-47-2 ]
YieldReaction ConditionsOperation in experiment
68% With bis(tri-tertiary-butylphosphine)palladium(0) In tetrahydrofuran; lithium hydroxide monohydrate for 12h; Alkaline conditions; Reflux; 1.5 5) Synthesis of Compound A After introducing Intermediate A-4 (17.7 g, 41.1 mmol), Intermediate A-3 (20 g, 68.5 mmol) and Pd(t-Bu3P)2 (0.14 g, 0.3 mmol) to an aqueous 2 M K2CO3 solution (60 ml) and THF (200 ml), the result was stirred under reflux for approximately 12 hours. After the reaction was finished, the result was cooled to room temperature, and an organic layer was separated from the reaction mixture solution. The organic layer was dried with magnesium sulfate, vacuum distilled and then recrystallized with Tol/EA to obtain Compound A (32.1 g, yield: 68%).MS[M]=690.7
  • 76
  • [ 863992-56-7 ]
  • [ 2245080-10-6 ]
  • [ 2254808-86-9 ]
YieldReaction ConditionsOperation in experiment
75% With bis(tri-tertiary-butylphosphine)palladium(0) In tetrahydrofuran; lithium hydroxide monohydrate for 12h; Alkaline conditions; Reflux; 2.3 3) Synthesis of Compound B After introducing Intermediate A-4 (13.4 g, 31.1 mmol), Intermediate B-2 (20 g, 68.5 mmol) and Pd(t-Bu3P)2 (0.14 g, 0.3 mmol) to an aqueous 2 M K2CO3 solution (60 ml) and THF (200 ml), the result was stirred under reflux for approximately 12 hours. After the reaction was finished, the result was cooled to room temperature, and an organic layer was separated from the reaction mixture solution. The organic layer was dried with magnesium sulfate, vacuum distilled and then recrystallized with Tol/EA to obtain Compound B (35.5 g, yield: 75%).MS[M]=690.2
  • 77
  • [ 863992-56-7 ]
  • [ 120173-41-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
10% With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In lithium hydroxide monohydrate; toluene at 95℃; for 24h; Schlenk technique; Inert atmosphere;
  • 78
  • [ 863992-56-7 ]
  • [ 36809-26-4 ]
  • [ 3964-04-3 ]
  • [ 2832111-05-2 ]
YieldReaction ConditionsOperation in experiment
76 % With palladium diacetate; calcium carbonate In dimethyl sulfoxide at 20℃; Inert atmosphere; 9 Example 9 (1) Dissolve 323 mg of 4-bromo-N,N-diphenylaniline in dimethyl sulfoxide and stir well at room temperature to obtain a 4-bromo-N,N-diphenylaniline solution with a concentration of 1mol/L;(2) 208 mg of 4-bromoquinoline was dissolved in dimethyl sulfoxide, fully stirred to obtain a 4-bromoquinoline solution with a concentration of 1mol/L;(3) Fully mix the 4-bromo-N,N-diphenylaniline solution and the 4-bromoquinoline solution, further ultrasonically stir, and add 100 mg of calcium carbonate to the resulting mixture, fill with nitrogen, and control the reaction The temperature is 20°C, and 430 mg of anthracene-9,10-bis(pinacolborane) and 2.24 mg of palladium acetate are added dropwise to the above reaction system. Ultrasound is carried out during the reaction, and the reaction is carried out for 48 hours. After that, the solvent is distilled off under reduced pressure to obtain The crude product was further separated and purified by an alumina chromatographic column with a dichloromethane-petroleum ether system (dichloromethane/petroleum ether, V/V=1:10), and finally dried in vacuo to obtain 416.65 mg of a yellow powder. The yield 76%, ie N,N-diphenyl-4-(10-(quinolin-4-yl)anthracen-9-yl)aniline (DPQATA, formula I-7).
  • 79
  • [ 863992-56-7 ]
  • [ 1159816-09-7 ]
  • [ 2933237-16-0 ]
YieldReaction ConditionsOperation in experiment
31.5 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; ethanol; water Reflux; iii.- 2-(9-anthryl)-5-(1H-pyrazol-1-yl)pyrazine (pypyr-anthra). General procedure: 1.00 g (4.5 mmol) of 9-anthraceneboronic acid pinacol ester, 1.52 g(6.75 mmol) of 2-bromo-5-(1H-pyrazol-1-yl)pyrazine (prepared as previouslyreported [28]) and 0.100 g of tetrakistriphenylphosphinepalladium(0) (Pd(PPh3)4) were mixed in 50 mL of 1,4-dioxane (Scheme 3). 3mL of 2.0 M water solution of potassium carbonate and 5 mL of absoluteethanol were added to the mix. The mixture was refluxed and stirred for48 h, being monitored by means of thin layer chromatography. Aftercooling, a crude solid product was obtained by means of solvent evaporationat reduced pressure.This crude product was purified by silica column chromatographyusing dichloromethane as the eluent. A yellow powder solid was isolatedafter fraction collection and solvent evaporation in a 49.6 % yield.
  • 80
  • [ 863992-56-7 ]
  • [ 1159816-09-7 ]
  • [ 2933237-19-3 ]
YieldReaction ConditionsOperation in experiment
31.5 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; ethanol; water Reflux; iii.- 2-(9-anthryl)-5-(1H-pyrazol-1-yl)pyrazine (pypyr-anthra). General procedure: 1.00 g (4.5 mmol) of 9-anthraceneboronic acid pinacol ester, 1.52 g(6.75 mmol) of 2-bromo-5-(1H-pyrazol-1-yl)pyrazine (prepared as previouslyreported [28]) and 0.100 g of tetrakistriphenylphosphinepalladium(0) (Pd(PPh3)4) were mixed in 50 mL of 1,4-dioxane (Scheme 3). 3mL of 2.0 M water solution of potassium carbonate and 5 mL of absoluteethanol were added to the mix. The mixture was refluxed and stirred for48 h, being monitored by means of thin layer chromatography. Aftercooling, a crude solid product was obtained by means of solvent evaporationat reduced pressure.This crude product was purified by silica column chromatographyusing dichloromethane as the eluent. A yellow powder solid was isolatedafter fraction collection and solvent evaporation in a 49.6 % yield.
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