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Chemical Structure| 13922-41-3
Chemical Structure| 13922-41-3
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Product Details of [ 13922-41-3 ]

CAS No. :13922-41-3 MDL No. :MFCD00019722
Formula : C10H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HUMMCEUVDBVXTQ-UHFFFAOYSA-N
M.W :171.99 Pubchem ID :254532
Synonyms :

Calculated chemistry of [ 13922-41-3 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 53.77
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 0.52
Log Po/w (MLOGP) : 1.35
Log Po/w (SILICOS-IT) : 0.34
Consensus Log Po/w : 0.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.328 mg/ml ; 0.00191 mol/l
Class : Soluble
Log S (Ali) : -2.56
Solubility : 0.474 mg/ml ; 0.00276 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.96
Solubility : 0.189 mg/ml ; 0.0011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 13922-41-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13922-41-3 ]

* 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.

  • Upstream synthesis route of [ 13922-41-3 ]
  • Downstream synthetic route of [ 13922-41-3 ]

[ 13922-41-3 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 13922-41-3 ]
  • [ 1698-16-4 ]
Reference: [1] Patent: WO2013/32297, 2013, A1,
[2] Patent: WO2013/73874, 2013, A1,
[3] Patent: KR2016/35448, 2016, A,
[4] Patent: KR2015/84657, 2015, A,
[5] Patent: KR101876777, 2018, B1,
[6] Patent: JP2015/189722, 2015, A,
  • 2
  • [ 1127647-91-9 ]
  • [ 13922-41-3 ]
  • [ 34160-40-2 ]
  • [ 1169702-61-7 ]
Reference: [1] Patent: US2010/204500, 2010, A1,
  • 3
  • [ 523-27-3 ]
  • [ 13922-41-3 ]
  • [ 26979-27-1 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 18, p. 3360 - 3364
  • 4
  • [ 13922-41-3 ]
  • [ 90-14-2 ]
YieldReaction ConditionsOperation in experiment
89% With 1,10-Phenanthroline; oxygen; potassium iodide; copper(ll) bromide In N,N-dimethyl-formamide at 80℃; for 20 h; General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBr2 (4.5 mg, 10 mol percent), 1,10-phen (7.2 mg, 20 mol percent) and DMF (2 mL). The mixture was stirred at 80 or 130 °C. After the completion of the reaction, the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel to give the product.
87% With iodine; potassium carbonate In acetonitrile at 80℃; for 9 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v
86% With perfluoroisopropyl iodide; copper; hydroquinone In N,N-dimethyl-formamide at 20℃; for 24 h; General procedure: (4-Nitrophenyl)boronic acid (0.067 g, 0.4 mmol), copper powder (0.0052 g, 0.08 mmol,), (CF3)2CFI (0.178 g, 0.6 mmol), and DMF (2 mL) were placed in a closed tube with a rubber stopper. The mixture was reacted at room temperature equipped with an air balloon for 24 h. The resulting suspension was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated to dryness. The crude product was purified by flash column chromatography on silica gel using petroleum ether/ethyl acetate = 20: 1 (v/v) as eluent to give 0.086 g of 2j as a light yellow solid (0.35 mmol, 87percent).
85% With copper(II) nitrate trihydrate; iodine In acetonitrile at 20℃; for 6 h; Sealed tube General procedure: 0.05 mmol Cu(NO3)2·3H2O, 1 mmol I2, 1 mmol arylboronic acids and 0.8 mL acetonitrile were added into an about 15 mL tube. Subsequently, the reaction tube was sealed to perform the reaction for 6 h without inert gas protection. Once the reaction time was reached, 10 mL water was added. The mixture was then extracted with dichloromethane (3 x 15 mL). The combined organic layers were washed with aqueous sodium hyposulfite, distilled water, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data.

Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1993 - 1995
[2] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
[3] Journal of Fluorine Chemistry, 2016, vol. 189, p. 59 - 67
[4] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660
[5] Catalysis Communications, 2013, vol. 32, p. 15 - 17
  • 5
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  • [ 85-46-1 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641
  • 6
  • [ 589-87-7 ]
  • [ 13922-41-3 ]
  • [ 204530-94-9 ]
YieldReaction ConditionsOperation in experiment
81% With sodium carbonate In water; toluene at 90℃; for 24 h; Inert atmosphere Under an argon gas atmosphere, 200.0 g (1.163 mol) of 1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 4-bromoiodobenzene, 26.9 g (23.3 mmol) of tetrakis(triphenylphosphine)palladium(0), 3.7 L of toluene and 1.74 L of aqueous solution of 2M sodium carbonate were added together, and stirred at 90 degrees C. for 24 hours. After the reaction was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. The organic phase thereof was washed by water and dried with magnesium sulfate, and the toluene was then distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 268 g of 1-(4-bromophenyl) naphthalene was obtained at an yield of 81percent.
81% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24 h; Inert atmosphere; Reflux 1.72 g (10 mmol) of Intermediate-2 and 2.83 g (10 mmol) of 1-bromo-4-iodobenzene were introduced under nitrogen and dissolved in 30 ml of toluene0.58 g (0.5 mmol) of Pd (PPh3) 4 and 15 ml (30 mmol) of 2M K2CO3 were added, respectively, and refluxed for 24 hours. After the completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, 150 ml of MC and 150 ml of H2O were added to extract the MC layer,Dried over MgSO4, concentrated and then columned with Hex: EA = 5: 1 to yield Intermediate-5 2.29 (81percent).
80% With potassium carbonate In tetrahydrofuran for 24 h; Heating / reflux 3-A. Production of compound 3a; [87] After l-bromo-4-iodobenzene (10 g, 35.35 mmol) and 1-naphthalene bromic acid(5.47 g, 31.82 mmol) were dissolved in anhydrous THF (100 mL), Pd(PPh3^ (1.2 g, 1.06 mmol) and 50 mL of 2M K CO aqueous solution were added and then refluxed for 24 hours. The organic layer was extracted by using ethyl acetate and water was removed with magnesium sulfate. The organic layer was filtered at reduced pressure and concentrated, and the solvent was removed. The resulting substance was purified by using column chromatography and then recrystallized in THF and ethanol to obtain a white solid compound 3a (8.0 g, 80percent).[88] MS [M + H] = 283
72% With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 90℃; for 1 h; Inert atmosphere Step 1-1:
Synthesis of 1-(4-bromophenyl)naphthalene
Synthesis Scheme (a-1) of Step 1-1 is shown.
Into a 3-L three-neck flask were put 47 g (0.28 mol) of 1-naphthaleneboronic acid and 82 g (0.29 mol) of 4-bromoiodobenzene, and 750 mL of toluene and 250 mL of ethanol were added thereto.
While the pressure was reduced, this mixture was degassed by being stirred.
After the degassing, the atmosphere in the flask was replaced with nitrogen.
To the solution was added 415 mL (2.0 mol/L) of a potassium carbonate solution.
The obtained mixture was degassed by being stirred while the pressure was reduced, and then, the atmosphere in the flask was replaced with nitrogen.
Into this were added 4.2 g (14 mmol) of tris(2-methylphenyl)phosphine and 0.7 g (2.8 mmol) of palladium(II) acetate.
This mixture was stirred under a nitrogen stream at 90° C. for an hour.
After the stirring, this mixture was allowed to cool to room temperature, and an aqueous layer of this mixture was extracted three times with toluene.
The extracted solution and an organic layer were combined and washed twice with water and washed twice with saturated saline.
Into this mixture was added magnesium sulfate, and the mixture was dried for 18 hours.
The obtained mixture was subjected to natural filtration to remove magnesium sulfate, and the filtrate was concentrated to obtain an orange liquid.
To this orange liquid was added 500 mL of hexane, and the obtained solution was filtrated through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855, the same applies to Celite described below and a repetitive description thereof is omitted) and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135, the same applies to Florisil described below and a repetitive description thereof is omitted).
The obtained filtrate was concentrated to give a colorless liquid.
Into the colorless liquid was added hexane, the obtained mixture was kept at -10° C., and a precipitated impurity was separated by filtration.
The obtained filtrate was concentrated to give a colorless liquid.
This colorless liquid was purified by distillation under reduced pressure to give a yellow liquid, and the yellow liquid was purified by silica gel column chromatography (developing solvent: hexane), whereby 56 g of an objective colorless liquid was obtained in a yield of 72percent.
72% With palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In ethanol; water; toluene at 90℃; for 1 h; Inert atmosphere To a 3 L three-neck flask were added 47 g (0.28 mol) of l -naphthaleneboronic acid and 82 g (0.29 mol) of 4-bromoiodobenzene and added 750 mL of toluene and 250 mL of ethanol. The mixture was degassed by being stirred while the pressure was being reduced, and after the degassing, the atmosphere in the flask was replaced with nitrogen. To the solution was added 415 mL of an aqueous solution of potassium carbonate (2.0 mol L). The mixture was degassed again by being stirred while the pressure was being reduced, and after the degassing, the atmosphere in the flask was replaced with nitrogen. Further, 4.2 g (14 mmol) of tri(o / ? -tolyl)phosphine and 0.7 g (2.8 mmol) of palladium(Il) acetate were added. This mixture was stirred at 90 °C for 1 hour under a nitrogen stream. After the stirring, the mixture was naturally cooled to room temperature, and the aqueous layer of the mixture was extracted three times with toluene. The resulting solution of the extract and the organic layer were combined and washed twice with water and twice with a saturated aqueous solution of sodium chloride. Then, magnesium sulfate was added, and the mixture was left still for 18 hours for drying. The mixture was subjected to gravity filtration to remove magnesium sulfate, and the resulting filtrate was concentrated to give an orange liquid. To the orange liquid was added 500 mL of hexane, and the resulting solution was purified through Celite and Florisil. The obtained filtrate was concentrated to give a colorless liquid. To the colorless liquid was added hexane, and the mixture was left still at -10 °C, and the precipitated impurities were separated by filtration. The resulting filtrate was concentrated to give a colorless liquid. The colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane) to give 56 g of a target colorless liquid in a yield of 72 percent
62% With potassium carbonate In ethanol; water; toluene at 90℃; for 4 h; Step 1: Synthesis of l-(4-bromophenyl)-naphthalene][0836]A synthetic scheme of l-(4-bromophenyl)-naphthalene in Step 1 is shown in the following (W-I). <n="270"/>[0838]In a 500-mL three-neck flask, 46g (160 mmol) of 4-bromoiodobenzene, 24 g (140 mmol) of 1-naphthaleneboronic acid, 45 mg (0.2 mmol) of palladium(II) acetate, and 60 mg (0.2 mmol) of tri(o-tolyl)phosphine were put, and 100 mL of toluene, 20 mL of ethanol, and 11 mL of a potassium carbonate solution (2 mol/L) were added to this mixture. This mixture was deaerated while being stirred under low pressure. After the deaeration, the mixture was stirred under a nitrogen atmosphere at 90 0C for 4 hours to be reacted.[0839]After the reaction, 500 mL of toluene was added to this reaction mixture, and this suspension was filtrated through Florisil and then Celite. The obtained filtrate was washed with water. Then, magnesium sulfate was added to remove moisture. This suspension was filtrated through Florisil and then Celite to obtain filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography(developing solvent, hexane). The obtained fraction was concentrated to obtain 25 g of an objective colorless transparent liquid at a yield of 62 percent.
62% With potassium carbonate; tris-(o-tolyl)phosphine In water; toluene at 90℃; for 4 h; Inert atmosphere In a 500-mL three-neck flask, 46g (160 mmol) of 4-bromoiodobenzene, 24 g (140 mmol) of 1-naphthaleneboronic acid, 45 mg (0.2 mmol) of palladium(II) acetate, and 60 mg (0.2 mmol) of tri(o-tolyl)phosphine were put, and 100 mL of toluene, 20 mL of ethanol, and 11 mL of a potassium carbonate aqueous solution (2 mol/L) were added to this mixture. This mixture was deaerated while being stirred under low pressure. After the deaeration, the mixture was stirred under a nitrogen atmosphere at 90 0C for 4 hours to be reacted. After the reaction, 500 mL of toluene was added to this reaction mixture, and this suspension was filtrated through Florisil and then Celite. The obtained filtrate was washed with water, and magnesium sulfate was added thereto to remove moisture. This suspension was filtrated through Florisil and then Celite to obtain filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent, hexane). The obtained fraction was concentrated to obtain 25 g of an objective colorless transparent liquid at a yield of 62 percent. A synthetic scheme of Step 2 is shown in (b-7) given below. An Rf value of the objective substance by a silica gel thin layer chromatography (TLC) (developing solvent, hexane) was 0.38 and that of 4-bromoiodobenzene was 0.57.
62% With potassium carbonate In ethanol; water; toluene at 90℃; for 4 h; Inert atmosphere Example 1; Synthesis Example 1; In this example, a synthesis method of 4-bromo-4'-(1-naphthyl)diphenylamine (abbreviation: BrNBA), which is represented by the following structural formula (100) is described.; Step 1: Synthesis of 1-(4-bromophenyl)-naphthalene; In a 500-mL three-neck flask, 46 g (160 mmol) of 4-bromoiodobenzene, 24 g (140 mmol) of 1-naphthaleneboronic acid, 45 mg (0.2 mmol) of palladium(II) acetate, and 60 mg (0.2 mmol) of tris(o-tolyl)phosphine were put, and 100 mL of toluene, 20 mL of ethanol, and 11 mL of a potassium carbonate solution (2 mol/L) were added thereto. This mixture was degassed while being stirred under reduced pressure. After that, the mixture was stirred under a nitrogen atmosphere at 90° C. for 4 hours to be reacted.After the reaction, 500 mL of toluene was added to the reaction mixture solution, and the resulting suspension was filtrated through Florisil (Catalog No. 540-00135, produced by Wako Pure Chemical Industries, Ltd.) and Celite (Catalog No. 531-16855, produced by Wako Pure Chemical Industries, Ltd.). The obtained filtrate was washed with water, and magnesium sulfate was added thereto to adsorb moisture. This suspension was filtrated through Florisil and Celite to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent: hexane). The obtained fraction was concentrated to obtain 25 g of a colorless transparent liquid which was a desired substance in a yield of 62percent. A reaction of the above synthesis method is shown in the following scheme (F-1). An Rf value of the desired substance by a silica gel thin layer chromatography (TLC) (developing solvent: hexane) was 0.38 and that of 4-bromoiodobenzene was 0.57.
60% With sodium carbonate In ethanol; water; toluene at 40℃; for 8 h; The following components were loaded into a 100-ml recovery flask, and the whole was stirred in a stream of nitrogen at 4O0C for 8 hours.Compound 1-1 (manufactured by SIGMA-ALDRICH ) : <n="54"/>344 rag (2 mmole)Compound 1-2 (manufactured by TOKYO CHEMICAL INDUSTRY, CO., LTD.): 566 rag (2 mmole)Pd (PPh3J4: 0.1 gToluene: 10 mlEthanol: 5 ml2-M aqueous solution of sodium carbonate:10 mlAfter the completion of the reaction, the crystal was separated by filtration, and was washed with water, ethanol, and toluene. The resultant crystal was dried in a vacuum at 1200C, and then, 340 mg of Compound 1-3 were obtained (yield: 60percent) .

Reference: [1] Patent: US2010/331585, 2010, A1, . Location in patent: Page/Page column 96
[2] Patent: KR2017/49295, 2017, A, . Location in patent: Paragraph 0137-0142
[3] Patent: WO2008/13399, 2008, A1, . Location in patent: Page/Page column 15
[4] Patent: US9419237, 2016, B2, . Location in patent: Page/Page column 65; 66
[5] Patent: KR2015/38093, 2015, A, . Location in patent: Paragraph 0476-0481
[6] Patent: WO2009/72587, 2009, A1, . Location in patent: Page/Page column 268-269
[7] Patent: WO2009/139358, 2009, A1, . Location in patent: Page/Page column 98-99
[8] Patent: US2011/71317, 2011, A1, . Location in patent: Page/Page column 28
[9] Patent: WO2007/72889, 2007, A1, . Location in patent: Page/Page column 52-53
[10] Patent: US2007/60777, 2007, A1, . Location in patent: Page/Page column 14
[11] Patent: EP1864965, 2007, A1, . Location in patent: Page/Page column 25
[12] Patent: EP1997799, 2008, A1, . Location in patent: Page/Page column 27
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  • [ 204530-94-9 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In tetrahydrofuran; water; toluene for 24 h; Reflux; Inert atmosphere Step 1: Synthesis of Intermediate (C)15 g (63 mmol) of 1,4-dibromobenzene, 7.66 g (44 mmol) of 1-naphthaleneboron acid, 17.58 g (127 mmol) of potassium carbonate, and 1.83 g (50 mmol) of tetrakis-(triphenylphosphine) palladium were suspended in a mixed solvent including 200 ml of tetrahydrofuran, 200 ml of toluene, and 50 ml of purified water, and heated and refluxed under a nitrogen atmosphere for 24 hours.The reaction fluid was cooled to room temperature, and separated into two layers. Then, the solvent of an organic layer thereof was removed under a reduced pressure to provide a fluid. The fluid was separated by column chromatography (hexane) to remove the solvent and to provide 15 g of a gel intermediate (C) at a yield of 83percent.
64% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; waterReflux The starting material, 1,4-dibromobenzene (30 g, 127 mmol) to THF (560 mL) after the dissolved, naphthalen-1-ylboronic acid (21.9 g, 127 mmol), Pd (PPh3) 4 (4.41 g, 3.82 mmol ), K2CO3 (52.7 g, 381 mmol), followed by the addition of water (280 mL), stirred and refluxed. When the reaction is complete, the ether was extracted with water, the organic layer was concentrated and then the next, the resulting product to the organic was dried with MgSO4 and concentrated to silicagel column and recrystallization. To obtain 23 g (Yield: 64percent)
Reference: [1] Patent: US2012/280221, 2012, A1, . Location in patent: Page/Page column 23-24
[2] Patent: KR2016/5944, 2016, A, . Location in patent: Paragraph 0238-0241
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  • [ 881913-20-8 ]
Reference: [1] Patent: EP2471772, 2012, A1,
[2] Patent: JP5750821, 2015, B2,
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  • [ 954137-48-5 ]
Reference: [1] Patent: WO2012/15265, 2012, A1,
[2] Patent: CN103524399, 2016, B,
[3] Patent: JP5781499, 2015, B2,
  • 10
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  • [ 400607-04-7 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 2 h; 9,10-Dibromo anthracene(5.04g, 15mmol), naphthalene1-boronic acid (1.72g, 10mmol), Pd (PPh3) 4 ([0344] 0.58 g, 0.5mmol), potassium carbonate (4.15g, 30mmol) and THF: H2O = 2: 1 solution was dissolved in 200ml At 80 was stirred for 2 hours under reflux. Thereafter 40ml H2O was added and the organic layer was dried 40ml ether obtained by extraction three times with magnesium sulfate, and the intermediate B-3 to the residue obtained by evaporation of the solvent purification by silica gel column chromatography (3.06g, 80percent yield ) it was obtained.
76.89% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 60℃; for 0.333333 h; Inert atmosphere In N2under the protection of the, air three times, the solvent is toluene/water = 3:1 (60 ml:20 ml), 2-naphthyl boronic acid (5.6g, 32 . 6mmol), 9,10- dibromoanthracene (11g, 32.6mmol), potassium carbonate (11.2g, 81 . 5mmol) at the same time adding to the above-mentioned three-mouth bottle, begins to stir, 30 min after, adding catalyst four triphenyl phosphine palladium (1.13g, 0 . 98mmol), air again after a time, the temperature rising to 60 °C reflux, the reaction time is 20h left and right.Processing process: TLC for detection, the diatomaceous earth ( helps filters ), DCM for washing, separating, the spin vaporization of solvent, funnel over silica gel, eluant: DCM/PE = 10:1 by the spin vaporization of the solution, after crystallization for heavy PE, filtration to obtain the product, the resulting white solid product in 50 °C bake 3h, get C-1 (9.6g, 76.8percent).
62.1% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 50 - 90℃; Inert atmosphere Under a nitrogen atmosphere, 500mlThree-neck flask 1-naphthalene boronic acid (7g, 0.0407mol) and 9,10-dibromo-anthracene (17.8g, 0.0529mol) for installation into a rear oil bath behind a 2M K2CO3 dissolved in THF and the solvent reflux sikimyeo 50 maintaining the temperature rises to Pd (PPh3) 4 catalyst 0.3g put back 80 ~ 90 temperature to sikimyeo allowed to react for about 16 to 24 hours. Extracted with dichloromethane (300ml), followed by the removal of water on the obtained organic extracts. Then, the solvent was evaporated, and to the organic phase, and separated by column chromatography using hexane-zero eluted G compound (9.7g, yield: 62.1percent) was obtained the, structure was confirmed by 1H-NMR.
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24 h; Inert atmosphere; Reflux 3.36 g (10 mmol) of 9,10-dibromoanthracene and 1.72 g (10 mmol) of Intermediate-2 were introduced under nitrogen and dissolved in 45 ml of toluene0.58 g (0.5 mmol) of Pd (PPh3) 4 and 15 ml (30 mmol) of 2M K2CO3 were added, respectively, and refluxed for 24 hours. After completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H2O were added to extract the MC layer,Dried over MgSO4, concentrated and then columned with Hex: MC = 3: 1 to yield Intermediate-8 2.38 (62percent).
42% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 100℃; for 12 h; Inert atmosphere Synthesis of 9-bromo-10-(naphthalen-1-yl)anthracene
A mixture of 40 g(119 mmol) of 9,10-dibromoanthracene, 20.5 g(119 mmol) of naphthalen-1-ylboronic acid, 1.38 g(1.2 mmol) of Pd(PPh3)4, 120 ml of 2M Na2CO3, 200 ml of EtOH and 600 ml toluene was degassed and placed under nitrogen, and then heated at 100° C. for 12 h.
After finishing the reaction, the mixture was allowed to cool to room temperature.
The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica to give product(19.2 g, 50 mmol, 42percent) as a yellow solid.

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  • [ 13922-41-3 ]
  • [ 1268954-77-3 ]
Reference: [1] Patent: EP2471772, 2012, A1,
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