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[ CAS No. 591-18-4 ] {[proInfo.proName]}

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Chemical Structure| 591-18-4
Chemical Structure| 591-18-4
Structure of 591-18-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 591-18-4 ]

CAS No. :591-18-4 MDL No. :MFCD00001043
Formula : C6H4BrI Boiling Point : -
Linear Structure Formula :- InChI Key :CTPUUDQIXKUAMO-UHFFFAOYSA-N
M.W : 282.90 Pubchem ID :11561
Synonyms :

Calculated chemistry of [ 591-18-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.86
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 3.7
Log Po/w (WLOGP) : 3.05
Log Po/w (MLOGP) : 3.95
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 3.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.48
Solubility : 0.00937 mg/ml ; 0.0000331 mol/l
Class : Moderately soluble
Log S (Ali) : -3.39
Solubility : 0.115 mg/ml ; 0.000407 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.2
Solubility : 0.0181 mg/ml ; 0.0000638 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 591-18-4 ]

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 [ 591-18-4 ]

* 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 [ 591-18-4 ]
  • Downstream synthetic route of [ 591-18-4 ]

[ 591-18-4 ] Synthesis Path-Upstream   1~56

  • 1
  • [ 110-85-0 ]
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Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 26, p. 4463 - 4466
  • 2
  • [ 109-97-7 ]
  • [ 591-18-4 ]
  • [ 107302-22-7 ]
Reference: [1] Green Chemistry, 2010, vol. 12, # 6, p. 1097 - 1105
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9680 - 9696
  • 3
  • [ 585-76-2 ]
  • [ 591-18-4 ]
YieldReaction ConditionsOperation in experiment
80% With N-iodo-succinimide; [4,4’-bis(tert-butyl)-2,2’-bipyridine]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl]phenyl]iridium(III) hexafluorophosphate; iodine; caesium carbonate In 1,2-dichloro-ethane at 50℃; for 24 h; Inert atmosphere; Irradiation; Sealed tube General procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), NIS (1.5mmol, 337.5 mg) and I2 (60 μmol, 20 molpercent) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry DCE was added through a syringer under argon.The tube was sealed with Parafilm Mr® and placed in an oil bath with a contact thermometer, andthe reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λmax = 455 nm).After 24 h or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and thesilica was washed with DCM) (50 mL). The filtrate was collected and the solvent was removed invacuo. The crude residue was purified by silica gel flash column chromatography to provide thetarget product (2). (Note: The reaction was very sensitive to moisture, and the yields sharplydecreased to less than 5percent when 0.01 equivalent of H2O was added to the reaction system).
61% With 1-iodo-3,5,5-trimethylhydantoin In tetrachloromethane for 15 h; Reflux; Irradiation [00216] A mixture of 3 -bromobenzoic acid (0.40 g, 2.0 mmol), l-iodo-3,5,5- trimethylhydantoin (0.80 g, 3.0 mmol), and CC (10 mL) was refluxed under irradiation with tungsten lamp for 15 h. The cold reaction mixture was washed with 1 M aq Na2S03 (2 x 5 mL), dried over Na2S04, filtered through short neutral alumina pad and concentrated in vacuo to give 0.35 g (61percent) of 3- bromoiodobenzene. The combine aq sodium sulfite washings were extracted with DCM (3 x 10 mL), carefully acidified with cone, hydrochloric acid to pH 2 and stirred at 0-5 °C for 2 h. The precipitated solid was filtered off, washed on the filter with cold water and dried in vacuo to recover 0.12 g (30percent) of 3- bromobenzoic acid. The combine DCM extracts were dried over Na2S04, filtered and concentrated in vacuo to obtain 0.21 g (75percent) of 3,5,5-trimethylhydantoin.
Reference: [1] Synlett, 2018, vol. 29, # 12, p. 1572 - 1577
[2] Patent: WO2015/68159, 2015, A2, . Location in patent: Paragraph 00215-00216
  • 4
  • [ 89598-96-9 ]
  • [ 591-18-4 ]
Reference: [1] Synlett, 1998, # 2, p. 141 - 142
  • 5
  • [ 1711-09-7 ]
  • [ 591-18-4 ]
Reference: [1] Nature Chemistry, 2018, vol. 10, # 10, p. 1016 - 1022
  • 6
  • [ 201230-82-2 ]
  • [ 150177-91-6 ]
  • [ 591-18-4 ]
  • [ 121-91-5 ]
  • [ 585-76-2 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 18, p. 4794 - 4795
  • 7
  • [ 691-37-2 ]
  • [ 1426083-16-0 ]
  • [ 591-18-4 ]
  • [ 176088-47-4 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 25, p. 8851 - 8854
  • 8
  • [ 1711-09-7 ]
  • [ 126261-84-5 ]
  • [ 591-18-4 ]
  • [ 52710-27-7 ]
Reference: [1] Nature Chemistry, 2018, vol. 10, # 10, p. 1016 - 1022
  • 9
  • [ 1711-10-0 ]
  • [ 66832-24-4 ]
  • [ 591-18-4 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 19, p. 4321 - 4328
  • 10
  • [ 1829-88-5 ]
  • [ 591-18-4 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1968, p. 819 - 824
  • 11
  • [ 108-36-1 ]
  • [ 591-18-4 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 16, p. 2703 - 2706
  • 12
  • [ 591-19-5 ]
  • [ 591-18-4 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 13
  • [ 63520-49-0 ]
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Reference: [1] Angewandte Chemie, 1977, vol. 89, p. 502 - 504
  • 14
  • [ 2060-89-1 ]
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Reference: [1] Angewandte Chemie, 1977, vol. 89, p. 502 - 504
  • 15
  • [ 139-02-6 ]
  • [ 81447-71-4 ]
  • [ 108-86-1 ]
  • [ 101-84-8 ]
  • [ 591-50-4 ]
  • [ 591-18-4 ]
  • [ 6876-00-2 ]
  • [ 71-43-2 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 14, p. 3917 - 3923
  • 16
  • [ 108-86-1 ]
  • [ 108-95-2 ]
  • [ 591-18-4 ]
  • [ 583-55-1 ]
  • [ 589-87-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 1167 - 1174
  • 17
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Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 18
  • [ 7553-56-2 ]
  • [ 63467-81-2 ]
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Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 19
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Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 20
  • [ 7553-56-2 ]
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Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 21
  • [ 7553-56-2 ]
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Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 22
  • [ 7553-56-2 ]
  • [ 20893-74-7 ]
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Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 23
  • [ 591-18-4 ]
  • [ 201230-82-2 ]
  • [ 22726-00-7 ]
YieldReaction ConditionsOperation in experiment
90% With ammonium hydroxide; 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane; palladium diacetate In toluene at 120℃; for 20 h; Autoclave General procedure: To a 45 mL glass-lined autoclave, 1 (0.5 mmol), Pd(OAc)2 (0.01mmol), CYTOP®292 (0.02mmol), aqueous ammonia (0.2 mL) and toluene (10 mL) were sequentially added. After sealing, the autoclave was purged three times with carbon monoxide and pressurized with 100 psi of CO. The resulting mixture was then heated at 100 °C for 20 h. The autoclave was removed from the oil bath and cooled to room temperature prior to the release of excess carbon monoxide. The reaction mixture was concentrated by rotary evaporator, and purified by flash chromatography on silica gel with a mixture of hexanes and ethyl acetate (2:1to 1:2) as the eluent to afford the products.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5496 - 5499
  • 24
  • [ 139-02-6 ]
  • [ 81447-71-4 ]
  • [ 108-86-1 ]
  • [ 101-84-8 ]
  • [ 591-50-4 ]
  • [ 591-18-4 ]
  • [ 6876-00-2 ]
  • [ 71-43-2 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 14, p. 3917 - 3923
  • 25
  • [ 591-18-4 ]
  • [ 625-99-0 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 18, p. 4794 - 4795
  • 26
  • [ 591-18-4 ]
  • [ 201230-82-2 ]
  • [ 62-53-3 ]
  • [ 63710-33-8 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In N,N-dimethyl-formamide at 100℃; for 8 h; Schlenk technique; Inert atmosphere General procedure: In a typical experiment a solution containing the palladiumcatalyst (with 6 mol Pd-content) was placed in a Schlenk-tube.Under argon, 0.2 mmol (22.5 l) iodobenzene (1), 0.5 mmol aminereagent, 0.7 mmol (100 l) triethylamine and 1 ml solvent wasadded and the atmosphere was changed to carbon monoxide. Thereaction mixture was heated with stirring in an oil bath at 100Cand was analysed by gas chromatography.
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2015, vol. 397, p. 150 - 157
  • 27
  • [ 591-18-4 ]
  • [ 1066-54-2 ]
  • [ 766-81-4 ]
Reference: [1] Patent: US2008/51395, 2008, A1, . Location in patent: Page/Page column 131
[2] Catalysis Communications, 2014, vol. 47, p. 40 - 44
  • 28
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  • [ 766-81-4 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5712 - 5719
[2] Chemical Communications, 2012, vol. 48, # 30, p. 3617 - 3619
[3] Chemistry Letters, 2013, vol. 42, # 10, p. 1128 - 1130
[4] Organic Letters, 2015, vol. 17, # 10, p. 2522 - 2525
[5] Organic Letters, 2017, vol. 19, # 19, p. 5182 - 5185
[6] Patent: US2018/339967, 2018, A1,
  • 29
  • [ 591-18-4 ]
  • [ 64-19-7 ]
  • [ 1878-67-7 ]
Reference: [1] ChemCatChem, 2014, vol. 6, # 6, p. 1589 - 1593
  • 30
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  • [ 75-03-6 ]
  • [ 2725-82-8 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 8, p. 2361 - 2364
  • 31
  • [ 624-92-0 ]
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  • [ 33733-73-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1996, vol. 33, # 2, p. 409 - 414
  • 32
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  • [ 591-18-4 ]
  • [ 29848-59-7 ]
Reference: [1] Organometallics, 2017, vol. 36, # 7, p. 1220 - 1223
  • 33
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  • [ 65685-01-0 ]
Reference: [1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: WO2018/52903, 2018, A1,
  • 34
  • [ 591-18-4 ]
  • [ 1066-54-2 ]
  • [ 3989-13-7 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 19, p. 5182 - 5185
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 19, p. 4096 - 4114
[3] Chinese Chemical Letters, 2016, vol. 27, # 6, p. 961 - 963
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 2, p. 630 - 639
[5] Chemistry - A European Journal, 2000, vol. 6, # 13, p. 2362 - 2367
[6] Organic letters, 2002, vol. 4, # 19, p. 3199 - 3202
[7] Journal of Organic Chemistry, 2000, vol. 65, # 18, p. 5712 - 5719
[8] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1499 - 1503
[9] Organic Letters, 2012, vol. 14, # 4, p. 1106 - 1109
[10] Chemical Communications, 2012, vol. 48, # 30, p. 3617 - 3619
[11] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5633 - 5645
[12] Chemistry Letters, 2013, vol. 42, # 10, p. 1128 - 1130
[13] Organic Letters, 2015, vol. 17, # 10, p. 2522 - 2525
[14] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 8281 - 8291
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YieldReaction ConditionsOperation in experiment
67.6%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1.5 h; Inert atmosphere
Stage #2: at -78 - 20℃;
500ml round bottom flask was placed 1-bromo-3-iodo-benzene (25.0g, 88mmol) was dissolved into 200ml of tetrahydrofuran. The reaction solution was cooled road -78 under a nitrogen atmosphere. A n-butyllithium (60.75ml, 97mmol) to the cooled solution was slowly added dropwise thereto for 30 minutes, the mixture was stirred for 1 hour at the same temperature. Trimethyl borate (11g, 106mmol) were added dropwise at the same temperature the mixture was stirred at room temperature overnight. It was acidified by dropwise addition of 2 normal hydrochloric acid to the reaction solution, which was stirred for 1 hour. Extraction with ethyl acetate was separated organic layer was concentrated under reduced pressure, crystallization was put in a cold n-hexane. Intermediate 11-a> was obtained. (12g, 67.6percent).
67.6%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1.5 h; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere
Insert the 1-bromo-3-iodo-benzene (25.0g, 88mmol) in 500ml round bottom flask was put in a 200ml tetrahydrofuranDissolved.The reaction solution was cooled road -78 under a nitrogen atmosphere.It was slowly added dropwise for 30 minutes n-butyllithium (60.75ml, 97mmol) to the cooled solution,It was stirred for 1 hour at the same temperature.Trimethyl borate (11g, 106mmol) were added dropwise at the same temperature the mixture was stirred at room temperature overnight. It was acidified by dropwise addition of 2 normal hydrochloric acid to the reaction solution, which was stirred for 1 hour. Ethyl acetate was extracted with Tay organic layer was separated and concentrated under reduced pressure, crystallized into the cold n-hexane it was obtained (12g, 67.6percent).
Reference: [1] Patent: KR2015/130206, 2015, A, . Location in patent: Paragraph 0862-0867
[2] Patent: KR2016/13678, 2016, A, . Location in patent: Paragraph 0324-0330
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Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7792 - 7793
[2] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 592 - 595
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  • [ 1692-25-7 ]
  • [ 4422-32-6 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere 1-bromo-3-iodobenzene (1.118 g, 3.95 mol) and 3-pyridine boronic acid (0.559 g, 4.54 mol) were added to a 100 mL three neck round bottom flask. To this flask, dioxane (20 mL) and aqueous K2CO3 (2 N, 20 mL) were added. The mixture was stirred and degassed with a steam of argon for 30 minutes. Then under argon atmosphere, 50 mg (0.04 mmol) of Pd(PPh3)4 (1percent) was added. The mixture was heated to 100° C. and stirred overnight. The next day, the solvent was removed by roto-evaporation and the residue was suspended into an equal amount of water (50 mL) and CH2Cl2 (50 mL). The organic layer was separated from aqueous layer and washed with brine (50 mL.x.3). After drying over Na2SO4, and removal of the drying agent, about 0.92 g of 3-(3-bromophenyl)pyridine product (100percent) was afforded. 1H NMR (400 MHz, CDCl3) 8.85 (s, 1H), 8.65 (d, 1H), 7.87 (d, 1H), 7.75 (s, 1H), 7.57-7.52 (m, 2H), 7.41-7.35 (m, 2H).
88% With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 18 h; Inert atmosphere; Reflux A mixture of 3-bromoiodobenzene (19.8 g, 70.0 mmol, pyridine-3- borononic acid (8.6 g, 70.0 mmol) in 1 ,2-dimethoxyethane (315 mL) and 2.0 M aqueous sodium carbonate (105 mL) was sparged with nitrogen for 30 minutes, then palladium acetate (393 mg, 1 .75 mmol) and triphenylphosphine (918 mg, 3.50 mmol) were added and the mixture was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (3 x 150 ml_). The combined organic layer was washed with water and brine (2 x 150 ml_ each), then dried over magnesium sulfate, filtered and concentrated to a dark brown oil. The crude product was purified by silica gel MPLC (0 - 90percent ethyl acetate in hexanes as eluent). The product fractions eluting when the gradient had reached 55 - 85percent ethyl acetate in hexanes were combined and concentrated by rotary evaporation to give 3-(3-bromophenyl)pyridine as a dark yellow oil (14.5 g, 88percent yield) having a purity of 97percent based on UPLC analysis. This material was taken directly to Step 2.
77% With sodium carbonate In 1,4-dioxane; water at 95℃; for 24 h; Inert atmosphere Example 14; Synthesis of Compound 31; A 100 mL, round-bottomed Schlenk flask equipped with a magnetic stir bar was charged with 1-bromo-3-iodobenzene (5.754 g, 20.3 mmol), 3-pyridyl boronic acid (2.5 g, 20.3 mmol), 25 mL of a 2 M aqueous solution of Na2CO3, and 25 mL of 1,4-dioxane. Tetrakis (triphenylphosphine) palladium (0.54 g, 0.5 mmol) was added, the mixture was degassed using five vacuum/nitrogen back-fill cycles, and then was heated to 95° C. for 24 hours with vigorous stirring. The reaction mixture was allowed to cool to room temperature and diluted with CH2Cl2. The organic layer was washed with 1N HCl, H2O, and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The resulting yellow solid was purified by column chromatography on silica gel. Eluent ethyl acetate/hexane (3/97) gave compound 31 as a pale yellow oil 3.6 g (77percent). 1H NMR (400 MHz, CDCl3) δ 8.82 (br s, 1H), 8.63 (m, 1H), 7.85 (m, 1H), 7.73 (m, 1H), 7.53 (m, 2H), 7.36 (m, 2H).
46% With sodium hydrogencarbonate In 1,4-dioxane; water at 90℃; for 24 h; 149] 3-(3-Bromophenyl)pyridine (lib): A solution of pyridine 3-boronic acid 51 (1.0 g, 8.14 mmol), 3-bromo-l-iodobenzene 50 (2.0 g, 7.07 mmol) and sodium bicarbonate (1.5 g, 17.7 mmol) in dioxane (16 niL) and water (4 mL) was purged with N2 for 5 min.Tetrakis(triphenylphosphine)palladium (400 mg, 0.35 mmol) was added and the mixture was heated at 90 0C for 24 hr. The solution was cooled and the volatile organics were evaporated. The residue was partitioned between EtOAc (50 mL) and water and the layers were separated. The organic layer was washed with water, dried (Na2SO4), and concentrated to give 2.2 g of yellow oil. The crude material was purified on an Analogix automated system (24 g column, 0- 30percent EtOAc/heptane) to provide 760 mg (46percent) of pure lib. Some impure material was set aside.

Reference: [1] Patent: US2010/331547, 2010, A1, . Location in patent: Page/Page column 13
[2] Patent: WO2014/130597, 2014, A1, . Location in patent: Page/Page column 59; 60
[3] Patent: US2009/289547, 2009, A1, . Location in patent: Page/Page column 36
[4] Patent: WO2011/11712, 2011, A1, . Location in patent: Page/Page column 40-41
[5] Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4181 - 4205
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Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 19, p. 6999 - 7008
  • 39
  • [ 591-18-4 ]
  • [ 73183-34-3 ]
  • [ 594823-67-3 ]
YieldReaction ConditionsOperation in experiment
69% With pyridine; cesium fluoride In dimethyl sulfoxide at 105℃; for 2 h; Inert atmosphere; Schlenk technique General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv) and bispinacolatodiboron (254 mg, 1 mmol, 2 equiv). Under an argon atmosphere, freshly distilled DMSO (0.4 mL), the appropriate aryl iodide (0.5mmol), and pyridine (0.4 to 1 equiv) were added successively. The reaction mixture was heated to 105 °C and stirred for 2 h under argon.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4759 - 4768
  • 40
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  • [ 569343-09-5 ]
Reference: [1] Patent: US2015/311446, 2015, A1,
  • 41
  • [ 591-18-4 ]
  • [ 926-62-5 ]
  • [ 139155-55-8 ]
YieldReaction ConditionsOperation in experiment
42%
Stage #1: at 20 - 40℃; for 3 h;
Stage #2: With water; ammonium chloride In diethyl ether; toluene
lsobutylmagnesium bromide (2M in diethyl ether, 26.5ml, 53mmol) was added over 30 minutes at room temperature to a solution of 1-bromo-3-iodobenzene (1Og, 35.3mmol) and tetrakis(triphenylphosphine)palladium (0) (1.1 g, 0.954mmol) in toluene (160ml). The reaction mixture became green and the temperature was not allowed to rise above 400C. The reaction mixture was then stirred at room temperature for three hours. Aqueous ammonium chloride solution (160ml) was then added (the reaction became red) and the mixture was extracted with diethyl ether (2x100ml). The organics were washed with more ammonium chloride (100ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude product was then purified by distillation to provide the title compound (boiling point 88°C under 25mmHg, 3.2Og, 42percent). 1H-NMR (400MHz, CDCI3) : δ = 0.90 (d, 6H), 1.85 (m, 1 H), 2.44 (d, 2H), 7.07 (d, 1 H), 7.14 (t, 1 H)1 7.30 (m, 2H).
Reference: [1] Patent: WO2006/120544, 2006, A1, . Location in patent: Page/Page column 45-46
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  • [ 591-18-4 ]
  • [ 151583-29-8 ]
Reference: [1] Inorganic Chemistry, 2016, vol. 55, # 5, p. 2345 - 2354
  • 43
  • [ 591-18-4 ]
  • [ 86-74-8 ]
  • [ 185112-61-2 ]
YieldReaction ConditionsOperation in experiment
98% With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; Carbazole 2.00 g (12.0 mmol), 1-bromo-3-iodobenzene, 2.02 mL (15.8mmol), copper (Cu) 2.29 g (36.0 mmol) of calcium carbonate and 4.98 g (36.0 mmol) of DMF in 30 mL insert heated at 130 It was stirred. After the completion of the reaction, it cooled to ambient temperature and diluted with ethyl acetate to a vacuum filter, and passed through a silica gelThe filtrate was concentrated under reduced pressure. Separating the product by silica gel column chromatography (ethyl acetate: n- hexane = 1: 20) to give the desired intermediate compound (C) 3.80 g (98percent yield).
90% With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; In a dry 2L three-necked flask, 42.3 g of m-bromo iodobenzene and 27.5 g of carbazole were added. Then dry and degassed 800 mL of toluene was added as a solvent. Add 43.2g of sodium tert-butoxide (3eq.), 0.67 g of palladium acetate (2percent mol) and 3.7 g of ligand 1, 1′-binaphthyl-2,2′-bisdiphenylphosphine (BINAP, 4percent mol). The temperature was raised to 110°C and the reaction ended overnight. Cool to room temperature Activated carbon adsorption, suction filtration, solvent removal, recrystallization with toluene and ethanol, 40.9 g of intermediate I are obtained (yield 90percent).
89% With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 24 h; Inert atmosphere 1-bromo-3 - iodo-benzene (145 ml, 53 mmol), carbazole (8.7 g, 52 mmol), copper powder (10.1 g, 159 mmol) and potassium carbonate (22 g, 159 mmol) dimethyl was dissolved in formamide (120 ml), it was stirred under argon for 24 hours in the presence of 130 . When complete the reaction, The reaction mixture was cooled to ambient temperature, filtered on Celite mukhyeo ethyl acetate. Filtered, poured in water, extracted with ethyl acetate, and wash the organic layer extracted with brine. The washed organic layer was dried over magnesium sulfate and purified by column chromatography (silica gel) to give the title compound (14.9 g, 89percent).
82.4% at 150℃; for 48 h; Inert atmosphere Synthesis example 3:; Synthesis of N-(3-bromophenyl)carbazole (compound 4); (4) Under nitrogen, carbazole (24.3 g, 1 eq.) is added to a flask together with 1 -bromo-3- iodobenzene (98percent; 75.3 g, 1.9 eq.), potassium carbonate (48.2 g, 2.5 eq.) and copper (1 .77 g, 0.1 eq.). The reaction is heated to 150°C and stirred at 150°C for 48 h. The mixture is cooled to room temperature and diluted with 150 ml. of methylene chloride. 100 mL of demineralized water are added to the mixture, which is stirred. Removal of the aqueous phase is followed by washing a further 2x with demineralized water (100 mL). The organic phase is dried over sodium sulfate and concentrated. The excess 1 -bromo-3-iodobenzene is distilled off under reduced pressure. LC (Si02; cyclohexane/ methylene chloride 95:5) gives 37.1 g of product (82.4percent yield).1H NMR (CD2CI2, 400 MHz): δ = 8.13 (d, 2H), 7.75 (s, 1 H), 7.61 (d, 1 H), 7.53 (d, 1 H), 7.49 (d, 1 H), 7.42 (m, 4H), 7.27-7.31 (m, 2H)
79% With 18-crown-6 ether; copper; potassium carbonate In N,N-dimethyl-formamide at 150℃; Inert atmosphere A mixture of 9-H carbazole (4.0 g, 24.1 mmol), 3-bromoiodobenzene (10.23 g, 36.1 mmol), copper (3.06 g, 48.2 mmol), potassium carbonate (13.3 g, 96.4 mmol), 18-crown-6 (636 mg, 2.41 mmol) and DMF (anhydrous, 50 mL) was degassed for about 40 minutes. The mixture was then further degassed by heating to about 150° C. overnight under argon. After cooling to room temperature (RT), solids from reaction mixture were then filtered off. The filtrate was then poured into dichloromethane (DCM) (250 mL) and then washed with water (3×200 mL). The organic layer was dried over sodium sulfate and loaded onto silica gel. A flash column (hexanes) gave 6.56 g (79percent yield) of product 1B; pure by HNMR.
78% With copper; potassium carbonate In Tetraethylene glycol dimethyl ether at 140℃; for 5 h; Under nitrogen flow, carbazole (7.00 g), 3-bromoiodobenzene (14.2 g), copper powder (2.66 g), potassium carbonate (5.79 g), and tetraglyme (10 ml) were stirred while heating to 140°C for 5 hr and then allowed to cool to room temperature. After the completion of the reaction, chloroform was added to the reaction solution, and the insoluble matter was removed by filtration. Chloroform contained in the filtrate was evaporated under reduced pressure, and the resulting matter was purified by silica-gel column chromatography (n-hexane/toluene = 4/1) and dried under reduced pressure to obtain a target compound 11 (10.5 g, yield: 78percent) as a colorless viscous liquid.
78% With copper(l) iodide; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 48 h; Inert atmosphere; Reflux In the reaction flask carbazole 3.0g, meta-bromoiodobenzene 10.15g, 2.39 g copper iodide, 4.95g of potassium carbonate and 40mL of dry xylene, the reaction was refluxed for 48 hours nitrogen, was added 50mL of water quench off the reaction, extracted with dichloromethane, the solvent was evaporated, purified by column chromatography to give a white colored final precipitate 9-(3-bromophenyl)-9H- carbazole 3.5g, 78percent yield.
70% With potassium phosphate; copper(l) iodide In 1,4-dioxane at 90℃; for 12 h; Inert atmosphere Under a nitrogen atmosphere (N2 purging), Compound 1G(10 g, 35.48 mmol), 0.6 equivalent of Compound 1H, 0.1 equivalent of CuI, 3.5 equivalents of diaminocyclohexane, and 4.0 equivalents of potassium phosphate were added to 1,4-dioxane(350 ml), and stirred in a 90° C. oil bath. After 12 hours, water was added to the reaction mixture, and extraction was performed. Then, purification was performed using a column using a developing solvent of MC:hexane (5:1) to obtain a white solid 11(7.97 g, yield 70percent).
69% With potassium phosphate; copper(II) iodide; rac-diaminocyclohexane In 1,4-dioxane for 16 h; Inert atmosphere; Reflux In 250mL three-necked flask, were added carbazole 16.72g, m-bromoiodobenzene 42.44g, cuprous iodide 1.9g, 1,2- diaminocyclohexane 3.42g, 42.4g anhydrous potassium phosphate and solvent 1 , 4-dioxane 160mL, N2 replaced three times, heated to reflux and the reaction stopped after 16h.Cooled to room temperature, filtered, and the filtrate was collected, purified by column chromatography (dichloromethane: n-hexane = 1: 1-1: 0), the target receives the solid product 22g (69percent).
35% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 16 h; Inert atmosphere; Reflux Sigma aldrich in nitrogen (http://www. Sigmaaldrich. Com /) carbazole yarn (50 g, 299. 0 mmol) of toluene 0. 5 L senses a rotation velocity of the disk to, herein 1-bromo-3-iodobenzene sigma aldrich yarn (101. 5 g, 358. 8 mmol), bis (dibenzylideneacetone) palladium (0) (5. 16 g, 8. 97 mmol), tris-tert butylphosphine (3. 02 g, 15. 0 mmol) and sodium tert-butoxide (34. 5 g, 358. 8 mmol) in 100 °C sequentially and at the reflux by heating at a 16. Complete after reaction solution at a water doesn't have any error frames, then dichloromethane (DCM) extraction of water to the MgSO4 anhydride after triggers number, filter and was, concentrating it under reduced pressure. Thus-obtained residue number intermediate that is forward separated into flash column chromatography I-2 (33. 3 g, 35percent) a obtained
1.9 g
Stage #1: With tri-tert-butyl phosphine; palladium diacetate In toluene at 20℃; for 1 h; Inert atmosphere
Stage #2: at 80℃; for 6 h; Inert atmosphere
250ml 3-neck round bottom flask was charged 1-3 (5g), palladium(0)diacetate (0.1g), tri-tert-butylphosphine (0.3g), put the toluene (100ml), 1 h on the atmosphere of argon at room temperature It was stirred. After the addition of potassium carbonate (7.2g), 3- bromo carbazole (6.3g) in the mixture was stirred at 80 °C for 6 hours. After the addition of water and extracted with ethyl acetate to give 1.9g the title 1-4 substituents through a separation column using hexane and the resulting material after removal of water.

Reference: [1] Patent: KR101593182, 2016, B1, . Location in patent: Paragraph 0427; 0430; 0438; 0439
[2] Patent: CN107686484, 2018, A, . Location in patent: Paragraph 0123-0128
[3] Patent: KR101622443, 2016, B1, . Location in patent: Paragraph 0109; 0110
[4] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
[5] Patent: WO2012/4765, 2012, A2, . Location in patent: Page/Page column 73-74
[6] Patent: US2013/75706, 2013, A1, . Location in patent: Paragraph 0074
[7] Patent: EP1820801, 2007, A1, . Location in patent: Page/Page column 82; 83
[8] Patent: CN103588770, 2016, B, . Location in patent: Paragraph 0046
[9] Organic Electronics: physics, materials, applications, 2011, vol. 12, # 6, p. 1025 - 1032
[10] Patent: US2018/166636, 2018, A1, . Location in patent: Paragraph 0119; 0120
[11] Patent: CN103951621, 2016, B, . Location in patent: Paragraph 0072; 0073; 0075; 0076
[12] Journal of Materials Chemistry C, 2014, vol. 2, # 31, p. 6333 - 6341
[13] RSC Advances, 2015, vol. 5, # 22, p. 17030 - 17033
[14] Patent: KR2016/91198, 2016, A, . Location in patent: Paragraph 0212
[15] Patent: US2010/187984, 2010, A1, . Location in patent: Page/Page column 121
[16] Chemistry of Materials, 2011, vol. 23, # 2, p. 274 - 284
[17] Advanced Materials, 2011, vol. 23, # 12, p. 1436 - 1441
[18] Journal of Materials Chemistry, 2012, vol. 22, # 15, p. 7239 - 7244
[19] Journal of Materials Chemistry, 2012, vol. 22, # 8, p. 3447 - 3456
[20] Patent: US2013/119367, 2013, A1, . Location in patent: Page/Page column
[21] Patent: WO2016/102413, 2016, A1, . Location in patent: Paragraph 0080
[22] Patent: KR2015/136713, 2015, A, . Location in patent: Paragraph 0081-0087
[23] Patent: WO2016/102414, 2016, A1, . Location in patent: Paragraph 0068
[24] Patent: JP5856161, 2016, B2, . Location in patent: Paragraph 0054
  • 44
  • [ 591-18-4 ]
  • [ 185112-61-2 ]
YieldReaction ConditionsOperation in experiment
82.4% With copper; potassium carbonate In dichloromethane; water Synthesis Example 3
Synthesis of N-(3-bromophenyl)carbazole (compound 4)
Under nitrogen, carbazole (24.3 g, 1 eq.) is added to a flask together with 1-bromo-3-iodobenzene (98percent; 75.3 g, 1.9 eq.), potassium carbonate (48.2 g, 2.5 eq.) and copper (1.77 g, 0.1 eq.).
The reaction is heated to 150° C. and stirred at 150° C. for 48 h.
The mixture is cooled to room temperature and diluted with 150 mL of methylene chloride.
100 mL of demineralized water are added to the mixture, which is stirred.
Removal of the aqueous phase is followed by washing a further 2* with demineralized water (100 mL).
The organic phase is dried over sodium sulfate and concentrated.
The excess 1-bromo-3-iodobenzene is distilled off under reduced pressure. LC (SiO2; cyclohexane/methylene chloride 95:5) gives 37.1 g of product (82.4percent yield).
1H NMR (CD2Cl2, 400 MHz): δ=8.13 (d, 2H), 7.75 (s, 1H), 7.61 (d, 1H), 7.53 (d, 1H), 7.49 (d, 1H), 7.42 (m, 4H), 7.27-7.31 (m, 2H)
Reference: [1] Patent: US2012/7063, 2012, A1,
  • 45
  • [ 591-18-4 ]
  • [ 32316-92-0 ]
  • [ 667940-23-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In tetrahydrofuran for 24 h; Heating / reflux 2- A. Production of compound 2a; [79] After l-bromo-3-iodobenzene (10 g, 35.35 mmol) and 2-naphthalene bromic acid(5.47 g, 31.82 mmol) were dissolved in anhydrous THF (100 mL), Pd(PPh ) (1.2 g, 1.06 mmol) and 50 mL of 2M K CO aqueous solution were added and then refluxed <n="17"/>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 2a (8.5 g, 85percent).[80] MS [M + H] = 283
76% With sodium carbonate In water; toluene for 24 h; Inert atmosphere; Reflux Under an argon gas atmosphere, 243 g (1.41 mol) of 2-naphthaleneboronic acid, 400 g (1.41 mol) of 3-bromoiodobenzene, 3.27 g (28.2 mmol) of tetrakis(triphenylphosphine)palladium(0), 6.4 L of toluene and 3.2 L of aqueous solution of 2M sodium carbonate were added together, and stirred while being refluxed for 24 hours. After the reaction was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was washed by water and dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 303 g of 2-(3-bromophenyl)naphthalene was obtained at an yield of 76percent.
Reference: [1] Patent: WO2008/13399, 2008, A1, . Location in patent: Page/Page column 14-15
[2] Patent: US2010/331585, 2010, A1, . Location in patent: Page/Page column 94-95
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 19, p. 4096 - 4114
  • 46
  • [ 1694-31-1 ]
  • [ 591-18-4 ]
  • [ 197792-52-2 ]
YieldReaction ConditionsOperation in experiment
84% With 2-Picolinic acid; copper(l) iodide; caesium carbonate In 1,4-dioxane at 70℃; Inert atmosphere General procedure: General procedure for the synthesis of α-arylacetic acid tert-butyl esters: A Schlenk tube was charged with aryl iodide (1.0mmol), CuI (9.5mg, 0.05mmol), 2-picolinic acid (12mg, 0.10mmol), and cesium carbonate (978mg, 3.0mmol). The tube was evacuated and backfilled with argon three times before tert-butyl acetoacetate (2.0mmol) and 2mL of 1,4-dioxane was added. The tube was immersed in an oil bath, and the reaction mixture was stirred at the indicated temperatures for 33–48h. The cooled mixture was partitioned between ethyl acetate and saturated NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with PE/EA=20:1 to 3:1) to provide the desired α-arylacetic acid tert-butyl esters.
Reference: [1] Tetrahedron, 2014, vol. 70, # 20, p. 3327 - 3332
  • 47
  • [ 591-18-4 ]
  • [ 870119-58-7 ]
Reference: [1] Chemistry of Materials, 2011, vol. 23, # 2, p. 274 - 284
[2] Journal of Materials Chemistry, 2012, vol. 22, # 8, p. 3447 - 3456
[3] Patent: US2013/75706, 2013, A1,
[4] RSC Advances, 2015, vol. 5, # 22, p. 17030 - 17033
[5] Patent: KR101622443, 2016, B1,
[6] Patent: CN103951621, 2016, B,
  • 48
  • [ 591-18-4 ]
  • [ 864377-33-3 ]
Reference: [1] Patent: KR2015/136713, 2015, A,
[2] Patent: CN103588770, 2016, B,
[3] Patent: CN107686484, 2018, A,
  • 49
  • [ 591-18-4 ]
  • [ 939430-30-5 ]
Reference: [1] Patent: US2010/331547, 2010, A1,
[2] Patent: WO2014/130597, 2014, A1,
  • 50
  • [ 591-18-4 ]
  • [ 881913-20-8 ]
Reference: [1] Patent: EP2471772, 2012, A1,
[2] Patent: JP5750821, 2015, B2,
  • 51
  • [ 591-18-4 ]
  • [ 1115023-84-1 ]
Reference: [1] Patent: EP2947071, 2015, A1,
[2] Patent: KR2016/11036, 2016, A,
[3] Patent: JP2016/88927, 2016, A,
[4] Patent: KR2016/19747, 2016, A,
[5] Patent: KR2015/135070, 2015, A,
[6] Patent: US2018/94000, 2018, A1,
  • 52
  • [ 288-13-1 ]
  • [ 591-18-4 ]
  • [ 294877-33-1 ]
YieldReaction ConditionsOperation in experiment
78% With potassium phosphate monohydrate; manganese(II) chloride tetrahydrate; (S,S)-1,2-diaminocyclohexane In water for 24 h; Reflux In a 500 ml round-bottomed flask, 10.0 g (147 mmol) pyrazole,2.91 g (14.7 mmol) of MnCl 2 .4H 2 O, 67.7 g (294 mmol) of K 3 PO 4 .H 2 O,62.3 g (220 mmol) of 1-bromo-3-iodobenzene, 3.35 g (29.4 mmol) of trans-1,2-diaminocyclohexane and 70 ml of water were added and refluxed for 24 hours.After completion of the reaction, the temperature was lowered to room temperature, and methylene chloride was added thereto, followed by filtration using Celite.The filtrate was concentrated under reduced pressure and then subjected to column purification using ethyl acetate and n-hexane as eluent. (25.6 g, yield 78percent).
51% With copper(l) iodide; (S,S)-1,2-diaminocyclohexane; potassium carbonate In 1,4-dioxane for 19 h; Reflux 1-bromo-3-iodobenzene (18.20 g, 64.3 mmol), 1H-pyrazole (4.38 g, 64.3 mmol), and (1S,2S)-cyclohexane-1,2-diamine (1.5 g, 12.9 mmol) in dioxane (400 mL) were placed into a 1 L round-bottomed flask. Copper(I) iodide (0.613 g, 3.22 mmol) and potassium carbonate (17.78 g, 129 mmol) were added, and the reaction mixture was stirred at reflux for 19 h.
The crude mixture was then filtered through a pad of celite.
The filtrate was diluted with 400 mL of dichloromethane, and was washed with water.
The organic layer was concentrated and chromatographed on silica gel with 5percent ethyl acetate in hexane to give 7.3 g (51percent) of 1-(3-bromophenyl)-1H-pyrazole as a white solid.
Synthesis of N-(3-(1N-pyrazol-1-yl)phenyl)-3-(1-(2,6-dimethylphenyl)-1H-imidazol-4-yl)-N-phenylaniline.
Reference: [1] Patent: KR101897044, 2018, B1, . Location in patent: Paragraph 0444-0445; 0448-0450
[2] Patent: EP2574613, 2013, A1, . Location in patent: Paragraph 0144
  • 53
  • [ 591-18-4 ]
  • [ 3842-55-5 ]
  • [ 864377-31-1 ]
YieldReaction ConditionsOperation in experiment
30%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1.5 h; Inert atmosphere
Stage #2: at 20℃; for 1.5 h; Inert atmosphere
To a round bottom flask, 1-bromo-3-iodo-benzene (60.0 g, 212 mmol), 480 mL of tetrahydrofuran were added and the temperature falls to -78° C under a nitrogen condition . After 30 minutes, 126 mL of 1.6 M n-butyllithium (202 mmol) was slowly added dropwise . After 1 hour, 2-chloro-4,6-diphenyl-1,3,5-triazine 62.4 g (233 mmol) was dissolved in 250 mL of tetrahydrofuran, after dropping a solution slowly comes to room temperature and then stirred for 30 minutes. After stirring for about 1 hour at room temperature, 2N hydrochloric acid was added dropwise to the reaction solution until the acid is an aqueous solution. The combined organic layer was then extracted, concentrated and then separated by column chromatography to give <4-a> 24.7g (yield 30percent).
Reference: [1] Patent: KR101554545, 2015, B1, . Location in patent: Paragraph 0365-0370
  • 54
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  • [ 864377-31-1 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10 h; Inert atmosphere; Reflux To a 1000 ml flask was added 30.0 g (83.51 mmol) of Intermediate L-1, 28.35 g (100.21 mmol) of 1-bromo-3-iodebenzene, 23.08 g (167.02 mmol) of potassium carbonate, Tetrakis (triphenylphosphine) palladium )) 4.83 g (4.18 mmol) in tetrahydrofuran(350 mL) and water (100 mL), and the mixture was heated under reflux in a nitrogen stream for 10 hours. The resultant mixture was added to 1500 mL of methanol and the crystallized solid was filtered, and then dichloromethane was added thereto. The resulting mixture was filtered through silica gel / celite, and the organic solvent was removed in an appropriate amount, and the filtrate was recrystallized from methanol to obtain 37.3 g of 83percent Yield).
Reference: [1] Patent: KR2016/121282, 2016, A, . Location in patent: Paragraph 0127-0131
  • 55
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  • [ 1268954-77-3 ]
Reference: [1] Patent: EP2471772, 2012, A1,
  • 56
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  • [ 1036378-83-2 ]
  • [ 1233200-57-1 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 80℃; for 12 h; Inert atmosphere Nitrogen environment in the compound I-8 (50 g, 140 mmol) and tetrahydrofuran (THF) 0.45 L dissolved after, here in 1-bromo-3-iodobenzene (43.7 g, 154 mmol) and tetrakis (triphenylphosphine) palladium (1.62 g and stirred into a 1.40 mmol). Into the potassuim carbonate (48.4 g, 350 mmol) in saturated water it was heated to reflux at 80 for 12 hours. After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM), and then removing water by anhydrous MgSO4 One was then filter, and concentrate under reduced pressure. The obtained residue was purified by flash column chromatography to give the compound I-15 (41.5 g, 77percent).
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 10 h; Reflux; Inert atmosphere 196.48 mmol) of Intermediate L-5, 72.26 g (255.42 mmol) of 1-bromo-3-iodebenzene, 54.31 g (392.96 mmol) of potassium carbonate, Pd (PPh3) ) Was added to 400 mL of tetrahydrofuran and 200 mL of water, and the mixture was heated under reflux for 10 hours under a nitrogen stream. The resulting mixture was added to 1500 mL of methanol, and the crystallized solid was filtered, and then dichloromethane was dissolved. The mixture was filtered through silica gel / celite, and an organic solvent was removed in an appropriate amount. The residue was recrystallized from methanol to obtain 3-bromo-5'-phenyl The yield of compound 3-bromo-5'-phenyl-1,1 ': 3,1 "-terphenyl (58.63 g, 77percent The results of the analysis are as follows.
Reference: [1] Patent: KR2015/117173, 2015, A, . Location in patent: Paragraph 0239-0241
[2] Patent: KR2016/19747, 2016, A, . Location in patent: Paragraph 0234-0237
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