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Chemical Structure| 128796-39-4
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Product Citations

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon , et al. DOI:

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer heterogeneous catalyst Suzuki−Miyaura coupling reaction size-selective reaction catalyst processing

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Product Details of [ 128796-39-4 ]

CAS No. :128796-39-4 MDL No. :MFCD00151855
Formula : C7H6BF3O2 Boiling Point : -
Linear Structure Formula :CF3(C6H4)B(OH)2 InChI Key :ALMFIOZYDASRRC-UHFFFAOYSA-N
M.W : 189.93 Pubchem ID :2734389
Synonyms :
Chemical Name :(4-(Trifluoromethyl)phenyl)boronic acid

Calculated chemistry of [ 128796-39-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.27
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.71
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 0.29
Consensus Log Po/w : 0.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.3
Solubility : 0.942 mg/ml ; 0.00496 mol/l
Class : Soluble
Log S (Ali) : -2.18
Solubility : 1.27 mg/ml ; 0.00668 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.18
Solubility : 1.26 mg/ml ; 0.00665 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.57

Safety of [ 128796-39-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 128796-39-4 ]

* 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 [ 128796-39-4 ]
  • Downstream synthetic route of [ 128796-39-4 ]

[ 128796-39-4 ] Synthesis Path-Upstream   1~44

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Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
  • 2
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  • [ 6011-14-9 ]
  • [ 2338-75-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 3
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Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641
  • 4
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  • [ 105-36-2 ]
  • [ 721-63-1 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 42, p. 8238 - 8241
[2] Chemical Communications, 2002, # 6, p. 622 - 623
  • 5
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Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 6
  • [ 121-43-7 ]
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  • [ 128796-39-4 ]
YieldReaction ConditionsOperation in experiment
54%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h;
Stage #2: at -78 - 20℃; for 12 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 1 h;
[Embodiment 4]; In this embodiment, a synthesis method of9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)anthracene (CF3CzPA) represented by a structural formula (42) will be described.; [Step 1] Synthesis of 9-bromo-10-(4-trifluoromethylphenyl)anthracene; (i) Synthesis of 4-trifluoromethylphenylboronic acid; A synthesis scheme of 4-trifluoromethylphenylboronic acid is shown in (E-I). [0282]1 ) n-BuLi, THF, -780C[0283] 33 g (0.15 mol) of 4-bromotrifluoromethylbenzen was put into a 500-mL three-neck flask, and nitrogen substitution in the system was carried out. Then, 200 mL of tetrahydrofuran (THF) was added thereto, and the mixture was stirred. This mixture solution was stirred at -78 0C, and 100 mL (0.16 mol) of n-butyllithium (1.6 mol/L) was dropped into the solution through a dropping funnel. After that, the obtained solution was stirred at the same temperature for 1 hour, and 22.3 mL (0.20 mol) of trimethyl borate was added to be stirred for about 12 hours while the reaction <n="96"/>temperature was allowed to gradually increase to the room temperature. Then, 100 mL of dilute hydrochloric acid (1 rnol/L) was added to the reaction solution, and the solution was stirred for 1 hour. A water layer of the mixture was extracted using ethyl acetate three times, the extracted solution and an organic layer were washed together one time using saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was filtrated naturally to remove magnesium sulfate, and the filtrate was condensed to obtain a solid. The solid was washed with chloroform, whereby 15 g of a white solid, which was a target matter, was obtained with the yield of 54 percent.
Reference: [1] Patent: WO2008/26614, 2008, A1, . Location in patent: Page/Page column 93-95
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 17, p. 2513 - 2523
[3] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922
[5] Journal of Organometallic Chemistry, 2017, vol. 846, p. 305 - 311
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Reference: [1] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[2] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[3] Organic Letters, 2005, vol. 7, # 21, p. 4757 - 4759
[4] Tetrahedron, 2004, vol. 60, # 25, p. 5373 - 5382
[5] Patent: US5739166, 1998, A,
[6] Chemistry - A European Journal, 2011, vol. 17, # 48, p. 13502 - 13509
[7] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[8] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[9] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[10] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
[11] Patent: WO2003/101381, 2003, A2, . Location in patent: Page 72-73
  • 8
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YieldReaction ConditionsOperation in experiment
62%
Stage #1: With hydrogenchloride; sodium nitrite In methanol; water at 0 - 5℃; for 0.5 h;
Stage #2: With tetrahydroxydiboron In methanol; water at 20℃; for 1 h;
General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv), followed by H2O (0.5 ml). This mixture was stirred 2 min,and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg ofNaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0–5 °C, followed by HCl (135 mg, 1.5 mmol, 3.0 equivalents) in MeOH (1.0 mL). This mixture was stirred 60min. H2O (10 mL) was added to reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layer was dried over Na2SO4, followed by evaporation to give the products.
Reference: [1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
  • 9
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  • [ 7732-18-5 ]
  • [ 98-56-6 ]
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YieldReaction ConditionsOperation in experiment
60%
Stage #1: With iodine; magnesium In tetrahydrofuran at 20 - 30℃; for 2.5 h;
Stage #2: With ammonium chloride In tetrahydrofuran at 0℃; for 1 h;
In 500 ml four-mouth reaction flask, add 5.76 g magnesium chips, then heating and drying under the protection of nitrogen. Then 0.2 g of iodine, 32 g bis(dimethylamino)chloroborane and 50 ml tetrahydrofuran were added to the reaction flask. Then start dropping 6 g of 4-chlorotrifluoromethylbenzene and 30 ml tetrahydrofuran mixed solution, stirring for half an hour. Continue to drop 30.1 g of 4-chlorotrifluoromethylbenzene and 150 ml tetrahydrofuran mixed solution. The solution temperature maintained at 20 - 30 degrees, after 2 hours adding was complete. Then the mixed solution was cooled to 0 degrees, add 100 ml saturated ammonium chloride solution, continuously stir for 1 hour. Allow to stand to separate the phases. To the aqueous phase, use 100 ml ethyl acetate to extract. The combined organic layer, for drying of magnesium sulfate, concentrated under reduced pressure. For the residue 150 mL65 °C of ethyl acetate to dissolve, then in 2 hours to cool down to room temperature, and then the 1 hours by adding 600 ml of normal hexane, stirring 3 hours, filter and get the 22.8 g white solid 4-trifluoromethylphenylboronic acid, yield 60percent.
Reference: [1] Patent: CN104311587, 2017, B, . Location in patent: Paragraph 0065; 0066; 0067
  • 10
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Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[3] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[4] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
  • 11
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YieldReaction ConditionsOperation in experiment
35% With magnesium In tetrahydrofuran; hexane; ethyl acetate EXAMPLE 52
Synthesis of 4-(trifluoromethyl)phenylboronic acid
An oven dried Schlenk tube was charged with magnesium turnings (766 mg, 31.5 mmol), evacuated, and backfilled with argon.
To the reaction vessel was added 10 mL of ether followed by 4-(trifluoromethyl)phenyl bromide (4.20 mL, 30.0 mmol).
The reaction mixture was stirred without external heating for 1 hour, during which time an exotherm occurred and then subsided.
The solution was diluted with ether (10 mL) and transferred via cannula to a flask containing triisopropylborate (13.8 mL, 60.0 mmol) in 1:1 THF/ether (20 mL) at -78° C.
The resulting reaction mixture was kept at -78° C. for 15 minutes and then was allowed to warm to room temperature.
After stirring at room temperature for 15 minutes, the reaction mixture was poured onto 2.0 M HCl (60 mL).
The mixture was transferred to a separatory funnel, extracted with ethyl acetate (60 mL), washed with water (60 mL), and brine (60 mL).
The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo.
The crude material was dissolved in 2:1 hexane/ethyl acetate (90 ml,) and activated charcoal was added.
The mixture was filtered and the product crystallized upon cooling.
The crystals were collected by filtration to afford 1.98 g (35percent) of pale yellow needles.
35% With magnesium In tetrahydrofuran; hexane; ethyl acetate Example 52
Synthesis of 4-(trifluoromethyl)phenylboronic acid
An oven dried Schlenk tube was charged with magnesium turnings (766 mg, 31.5 mmol), evacuated, and backfilled with argon.
To the reaction vessel was added 10 mL of ether followed by 4-(trifluoromethyl)phenyl bromide (4.20 mL, 30.0 mmol).
The reaction mixture was stirred without external heating for 1 hour, during which time an exotherm occurred and then subsided.
The solution was diluted with ether (10 mL) and transferred via cannula to a flask containing triisopropylborate (13.8 mL, 60.0 mmol) in 1:1 THF/ether (20 mL) at -78° C.
The resulting reaction mixture was kept at -78° C. for 15 minutes and then was allowed to warm to room temperature.
After stirring at room temperature for 15 minutes, the reaction mixture was poured onto 2.0 M HCl (60 mL).
The mixture was transferred to a separatory funnel, extracted with ethyl acetate (60 mL), washed with water (60 mL), and brine (60 mL).
The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo.
The crude material was dissolved in 2:1 hexane/ethyl acetate (90 mL) and activated charcoal was added.
The mixture was filtered and the product crystallized upon cooling.
The crystals were collected by filtration to afford 1.98 g (35percent) of pale yellow needles.
Reference: [1] Patent: US6307087, 2001, B1,
[2] Patent: US2004/171833, 2004, A1,
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Reference: [1] Patent: US6303593, 2001, B1,
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  • [ 23287-26-5 ]
  • [ 145797-53-1 ]
  • [ 128796-39-4 ]
Reference: [1] Patent: US2003/109700, 2003, A1,
[2] Patent: US6197798, 2001, B1,
  • 14
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  • [ 98-56-6 ]
  • [ 128796-39-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
  • 15
  • [ 873066-23-0 ]
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Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 48, p. 13502 - 13509
[2] Journal of the American Chemical Society, 2013, vol. 135, # 4, p. 1264 - 1267
[3] Chemistry - A European Journal, 2013, vol. 19, # 46, p. 15565 - 15571
  • 16
  • [ 98-56-6 ]
  • [ 128796-39-4 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[2] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
  • 17
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, p. 715 - 720
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  • [ 98-08-8 ]
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Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[3] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
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Reference: [1] ChemCatChem, 2018, vol. 10, # 19, p. 4253 - 4257
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Reference: [1] Synthesis (Germany), 2017, vol. 49, # 4, p. 736 - 744
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7431 - 7441
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  • [ 1423-26-3 ]
Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
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Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
[3] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
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Reference: [1] Journal of Organometallic Chemistry, 2007, vol. 692, # 20, p. 4244 - 4250
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  • [ 53473-36-2 ]
Reference: [1] Synlett, 2011, # 17, p. 2517 - 2520
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  • [ 84392-17-6 ]
YieldReaction ConditionsOperation in experiment
74.55% With 20% palladium hydroxide-activated charcoal; sodium carbonate In water at 80 - 90℃; for 6 h; 2-Iodobenzoic acid (100 gm, 0.4032 moles) , 4-(Trifluoromethyl)phenyl boronic acid (99.55 gm, 0.524 moles), sodium carbonate (164 gm, 1.55 moles) and 20 percent palladium hydroxide on carbon (15 gm) in water (3.0 L) was heated to 80-90°C for 6 hrs. The progress of the reaction was monitored by HPLC. After completion of the reaction the reaction mass was cooled 70-80°C and filtered through hyflow bed. The filtrate was cooled to room temperature and the pH was adjusted to 1-2 with hydrochloric acid. The precipitated solid was filtered and washed with 1.0 L water. The solid was dissolved in 376 ml ethanol at 60-70°C and charcolised. The solution was filtered through hyflow bed at 60°C and washed with 180 mL hot ethanol. Water (1.086 L ) was added to the filtrate at 50 -60°C and the precipitated solid was cooled to room temperature. The solid was filtered and dried in air oven for 12 hrs at 60°C to afford 80 gm of 4'- (Trifluoromethyl)biphenyl-2-carboxylic acid as a white solid (Yield 74.55 percent, HPLC purity 99.98 percent).
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 25, p. 4225 - 4229
[2] Patent: WO2016/55934, 2016, A1, . Location in patent: Paragraph 0134
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Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4677 - 4687
[2] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6523 - 6526
[3] Organic Letters, 2014, vol. 16, # 12, p. 3216 - 3219
[4] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 911 - 919
[5] Organic Letters, 2015, vol. 17, # 18, p. 4550 - 4553
[6] Organic Letters, 2018, vol. 20, # 5, p. 1316 - 1319
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Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 19, p. 8960 - 8967
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YieldReaction ConditionsOperation in experiment
75% With sodium carbonate In water; toluene The title compound was made as described in general procedure D using 4-bromo benzoic acid [(10G,] 49.4 mmol), 4-trifluoromethyl phenylboronic acid [(14.] 17g, 74.61 mmol), palladium tetrakis-triphenylphosphine (5.7g, 4.974 [MMOL)] and [2N NA2C03 AQ. SOLUTION] (150 mL, 149.2 [MMOL)] in 500 ml of Toluene. After the reaction is complete, the reaction mixture was neutralized with 2N HCI then filtered. The resulting solid was dissolved in ethyl acetate then passed through a short column of silica gel giving 9.7 g (75percent) of the compound as a white solid.
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 34, p. 5751 - 5754
[2] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
[3] Patent: WO2004/14844, 2004, A2, . Location in patent: Page 179; 181
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 20, p. 4939 - 4952
[5] Journal of Medicinal Chemistry, 1997, vol. 40, # 20, p. 3144 - 3150
[6] Tetrahedron Letters, 2004, vol. 45, # 29, p. 5661 - 5663
[7] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 2, p. 750 - 758
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YieldReaction ConditionsOperation in experiment
86% With Pd/C; potassium carbonate In water at 110℃; for 48 h; General procedure: The Ni and Pd carbon aerogels were always sinked in water 24 h before their use as catalysts and kept in the same solvent.Catalytic reactions: In a 100 mL three necked round-bottom flask, arylboronic acid (15 mmol), aryl halide (10 mmol) and K2CO3 (2.76 g, 20 mmol) were dissolved in 20 mL of H2O. Then, Ni or Pd carbon aerogel (0.1 mmol, 1 mol percent) was added to the mixture and the reaction was carried out under reflux (110 °C), in the presence of air and mechanical stirring. Periodic sampling of the reaction media was made to analyze the reaction evolution by GC and 1H NMR measurements. The liquid phase was decanted and the carbon aerogel was washed with water. This water extracts and the reactive solution were mixed together and acidified until pH 1 to cause the precipitation of the final product. The solid was filtrated, washed with water and dried. The pieces of aerogel were washed with AcOEt, with water and were kept submerged in this solvent before reused.
Reference: [1] Green Chemistry, 2010, vol. 12, # 1, p. 150 - 158
[2] Tetrahedron, 2012, vol. 68, # 32, p. 6517 - 6520
[3] Patent: WO2004/81005, 2004, A1, . Location in patent: Page 135-136
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YieldReaction ConditionsOperation in experiment
96%
Stage #1: at 70℃; for 0.25 h;
Stage #2: With water; sodium carbonate In propan-1-ol for 1 h; Reflux
Step A:
4'-(trifluoromethyl)biphenyl-4-carbaldehyde
A round bottom flask was charged with 4-bromobenzaldehyde (69.6 g, 376 mmol), 4-(trifluoromethyl)phenylboronic acid (75.0 g, 395 mmol) and 1-propanol (627 mL).
The reaction mixture was stirred for 15 minutes at 70° C. until a clear solution was obtained.
The resulting solution was treated with triphenylphosphine (888 mg, 3.38 mmol), palladium(II) acetate (256 mg, 1.13 mmol), 2M sodium carbonate (226 mL, 451 mmol) and water (138 mL).
The reaction was heated at reflux for 1 hour, open to air.
Water (900 mL) was then added and the reaction was cooled to 7° C. in an ice bath.
The reaction was thoroughly stirred for 30 minutes until the title compound precipitated out.
The mixture was then filtered and the solid washed with cold water (~600 mL).
The solid was then solubilized in diethylether (500 mL) and filtered through a pad of celite and silica, rinsing with diethylether (2*500 mL).
Removal of the solvent under reduced pressure afforded 4'-(trifluoromethyl) biphenyl-4-carbaldehyde (90.0 g, 96percent) as a pure white solid. 1H NMR (400 MHz, CDCl3, δ): 7.75 (s, 4H) 7.76-7.79 (m, 2H) 7.96-8.04 (m, 2H) 10.10 (s, 1H). MS (M+1): 250.3.
94% With tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane; water at 20 - 70℃; for 2 h; Preparation 5; (R,S)-1-(4'-Trifluoromethyl-biphenyl-4-yl)-ethano; Step A. 4'-Trifluoromethyl-biphenyl-4-carbaldehyde; To an ambient temperature solution of 4- (trifluoromethyl)phenylboronic (4.64 g, 24.43 mmol) in dioxane/water (15/15 mL) is added 4-bromo-benzaldehyde (4.42 g, 22.21 mmol), tetrabutylammonium bromide (7.16 g, 22.21 mmol, potassium carbonate (7.67 g, 55.53 mmol) and is degassed for 10 min. Palladium (II) (748 mg, 1.11 mmol) is added and the reaction mixture is heated to 70 °C. After 2 h TLC (20percent EtOAc/hexane) indicates complete consumption of starting material. The reaction is cooled to room temperature diluted with water and extracted with EtOAc (3 x 200 mL). The combined organic extracts are washed with brine, dried (MgS04), filtered, concentrated and chromatographed (330 g Si02, 5percent EtOAc/Hexanes) to yield the title compound (5.54 g, 94percent). 1NMR (400MHz, CDCl3) 8 ppm: 10.09 (s, 1H), 8.01-8.00 (m, 1H), 7.99-7.98 (m, 1H), 7.78-7.75 (m, 2H), 7.74 (s, 4H); Preparation 31 (R,S)-1-(4'-Trifluoromethyl-biphenyl-4-yl)-ethanol Step A. 4'-Trifluoromethyl-biphenyl-4-carbaldehyde To an ambient temperature solution of 4- (trifluoromethyl)phenylboronic (4.64 g, 24.43 mmol) in dioxane/water (15/15 mL) is added 4-bromo-benzaldehyde (4.42 g, 22.21 mmol), tetrabutylammonium bromide (7.16 g, 22.21 mmol, potassium carbonate (7.67 g, 55.53 mmol) and degassed for 10 min. Palladium(II) acetate (748 mg, 1.11 mmol) is added and the reaction mixture is heated to 70 °C. After 2 h TLC (20percent EtOAc/hexane) indicates complete consumption of starting material. The reaction is cooled to room temperature diluted with water and extracted with EtOAc (3 x 200 mL). The combined organic extracts are washed with brine, dried (MgS04), filtered, concentrated and chromatographed (330 g Si02, 5percent EtOAc/Hexanes) to yield the title compound (5.54 g, 94percent). 1NMR (400MHz, CDCl3) No. ppm: 10.09 (s, 1H), 8.01-8.00 (m, 1H), 7.99-7.98 (m, 1H), 7.78-7.75 (m, 2H), 7.74 (s, 4H).
89% With tetrabutylammomium bromide; palladium diacetate; potassium carbonate In 1,4-dioxane; water at 70℃; for 3 h; Inert atmosphere Bromobenzaldehyde (1 eq, 0.95 mmol), 4-(Trifluoromethyl) phenylboronic acid (1.1 eq, 1.05 mmol), palladium (II) acetate, TBAB (1 eq, 0.95 mmol) and K2CO3 (2.5 eq, 2.37 mmol) were dissolved in a water/dioxane mixture (1/1, ν/ν, 1.5/1.5 mL) which was further deoxygenated three times (vacuum/ar). Palladium (II) acetate (0.05 eq, 0.05 mmol) was then added to the solution and the reaction mixture was heated to 70°C under stirring and argon for 3h. Water was added followed by extraction with EtOAc (3 x 10mL). The organic phases were washed with saturated NaCl then dried and filtered. After removal of the solvent, the remaining paste was purified using column chromatography (silica gel, 95/5 Hex/EtOAc) to obtain the desired compound (Rf = 0.35) as a colourless solid (210 mg, 89percent).1H NMR (CDCl3) δ: 10.09 (s, 1H), 7.99 (m, 2H), 7.77 (m, 2H), 7.74 (m, 4H).
86% With C22H24Cl2N6O2Pd2; potassium carbonate In ethanol; water for 4 h; Reflux General procedure: In a 10 mL glass tube containing a Teflon-coated stir bar was placed p-bromobenzaldehyde 2e (0.05 g, 0.27 mmol, 1 equiv), phenylboronic acid 1a (0.05 g, 0.40 mmol, 1.5 equiv), 2M K2CO3 (0.33 mL, 0.67 mmol, 2.5 equiv), 4-AAP-Pd(II) (0.28 mg, 0.3 mol percent Pd) and EtOH (2 mL). The mixture was stirred at reflux for 4 h. After cooling, the mixture was diluted with ether Et2O (5 mL), washed with sat. aq. NaHCO3 (3 mL), brine (3 mL) and dried over Na2SO4. Evaporation of the solvent and purification of the residue over a silica gel column (Hex: AcOEt 90:10), furnished the biphenyl 3q.
82.7% With C14H8F6O4; nickel trifluoroacetate; potassium carbonate; triphenylphosphine; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In water at 80℃; for 18 h; Green chemistry General procedure: A 50mL round-bottomed flask was charged with aryl halides (0.5 mmol), arylboronic acid (0.6 mmol), K2CO3 (1.25 mmol), Ni(TFA)2 (0.025 mmol), β-diketone ligand (0.05 mmol), PPh3 (0.05 mmol), 1.5 g of the ionic liquid (IL) and 0.5 g of H2O. Then, the mixture was stirred at 80 open to the atmosphere. The reaction was monitored by TLC and then stopped after the starting material was completely consumed. Next, the mixture was diluted with water (10 mL) and extracted with ether (310 mL). The combined organic layers were washed with brine (310 mL), dried over MgSO4, and concentrated in vacuum. The cross coupling products were not the only product of the reaction. A small amount of homo-coupled products and removal boron product from boric acids were observed. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate, 10:1).
82.9% at 90℃; for 6 h; General procedure: A mixture of compound 1 (3g, 16.21mmol), phenylboronic acid (2.57 g, 21.08 mmol), anhydrous potassium carbonate (K2CO3) (3.36 g, 24.32 mmol), tetrakistriphenylphosphine palladium (Pd(PPh3)4) 93.69 mg, 81.07 μmol) and PEG400 (18 ml) were poured into a 50 mL reaction vial and continued stirring at 90 °C about 6 h, the reaction mixture was added with distilled water, and extracted with ethyl acetate (3 × 150 mL). The organic extracts were dried with anhydrous Na2SO4, filtered and concentrated by rotary evaporation. The crude residue was purified by column chromatography (eluent: petroleum ether and ethyl acetate) to obtain the pure product as a white solid 2b.
77% With sodium carbonate In 1,2-dimethoxyethane; water at 20℃; for 20 h; Heating / reflux A 3 L 3-neck flask fitted with top stirrer, condenser and argon inlet/outlet was charged with 4-trifluoromethylbenzene boronic acid (90.0 g, 0.474 mol), 4- bromobenzaldehyde (83.29 g, 0.450 mol) and 1,2-dimethoxyethane (1.3 L), followed by 2M aqueous sodium carbonate (474 mL) and palladium acetate (5.32 g, 0.0237 mol). The stirring mixture was heated to reflux for 4 h under argon, then allowed to cool to room temperature over 16 h. The reaction mixture was filtered through hyflo. The filtrate was diluted with saturated brine and extracted 3x with ethyl acetate. The combined extracts were dried over magnesium sulfate and filtered through hyflo, giving a clear orange filtrate which was evaporated to a solid (ca. 120g, crude). Flash chromatography (silica, 10-50percent dichloromethane in pet. ether, 10percent steps) gave a white solid which dissolved in hexane (500mL) on boiling. Crystallisation, finally in ice, gave the title compound as a solid which was filtered off, washed with ice cold hexane and dried, (86.33g, 77percent). 'H-NMR (CDCl3) 6 7.77-8. 03 (8H, m), 10.09 (1H, s).
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 110℃; for 24 h; Inert atmosphere The preparation method of the biphenyl compound is:4.625 g (25 mmol) p-bromobenzaldehyde, 9.495 g (50 mmol)P-trifluoromethylbenzeneboronic acid,1.445 g (1.25 mmol) of tetrakis(triphenylphosphine)palladium, 13.8 g (100 mmol) of potassium carbonate,100 mL of ethylene glycol dimethyl ether and 15 mL of water are mixed.Nitrogen was pumped out three times and reacted at 110 degrees for 24 hours.After the reaction is completed, it is extracted with dichloromethane, and the organic phase is washed with water.Washed with saturated saline,Dry over anhydrous magnesium sulfate,The product was isolated by column chromatography (3.878 g).The yield was about 62percent.
55% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 12 h; Inert atmosphere 4-bromobenzaldehyde 1a (1.60 g, 8.8 mmol),4-(trifluoromethyl)phenylboronic acid 1b (2.0 g, 10.5 mmol), fourTriphenylphosphine palladium (508mg, 0.44mmol)And sodium carbonate (2.33g, 22.0mmol)Soluble in a mixed solution of 34mL ethylene glycol dimethyl ether and water (V/V=15/2),The reaction was carried out at 90° C. under argon protection for 12 hours. The reaction solution was concentrated under reduced pressure and 200 mL of water was added.The mixture was extracted with ethyl acetate (200 mL×3), and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: System A).4'-(trifluoromethyl)-[1,1'-biphenyl]-4-carbaldehyde 1c (1.19 g, white solid) was obtained, yield: 55.0percent.

Reference: [1] Patent: US2012/165343, 2012, A1, . Location in patent: Page/Page column 15
[2] Applied Organometallic Chemistry, 2012, vol. 26, # 9, p. 478 - 482
[3] Patent: WO2005/118542, 2005, A1, . Location in patent: Page/Page column 43; 55-56
[4] Green Chemistry, 2011, vol. 13, # 1, p. 169 - 177
[5] ChemMedChem, 2016, p. 2194 - 2204
[6] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 4, p. 787 - 792
[7] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2821 - 2826
[8] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2975 - 2990
[9] Catalysis Communications, 2014, vol. 58, p. 154 - 157
[10] Tetrahedron Letters, 2018, p. 681 - 686
[11] Patent: WO2003/87088, 2003, A2, . Location in patent: Page/Page column 18
[12] Patent: CN108484412, 2018, A, . Location in patent: Paragraph 0116; 0117; 0118; 0119
[13] Patent: CN107759522, 2018, A, . Location in patent: Paragraph 0147; 0152; 0153-0155
[14] Patent: EP2725024, 2014, A1, . Location in patent: Paragraph 0125; 0126
[15] Patent: US2014/171431, 2014, A1, . Location in patent: Paragraph 0471; 0472
[16] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 453 - 462
[17] Angewandte Chemie - International Edition, 2018, vol. 57, # 17, p. 4622 - 4626[18] Angew. Chem., 2018, vol. 130, # 17, p. 4712 - 4716,5
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  • [ 90035-34-0 ]
Reference: [1] New Journal of Chemistry, 2016, vol. 41, # 1, p. 372 - 376
[2] Organic Process Research and Development, 2012, vol. 16, # 1, p. 117 - 122
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  • [ 90035-34-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 24, p. 6959 - 6963[2] Angew. Chem., 2016, vol. 128, # 24, p. 7073 - 7077,5
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  • [ 90035-20-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 7, p. 1726 - 1729
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  • [ 343604-24-0 ]
Reference: [1] Patent: WO2005/118542, 2005, A1, . Location in patent: Page/Page column 45-46
[2] ChemMedChem, 2016, p. 2194 - 2204
[3] Archiv der Pharmazie, 2005, vol. 338, # 1, p. 9 - 17
[4] Pharmazie, 2003, vol. 58, # 12, p. 854 - 856
[5] Organic Letters, 2011, vol. 13, # 5, p. 952 - 955
[6] Angewandte Chemie - International Edition, 2018, vol. 57, # 17, p. 4622 - 4626[7] Angew. Chem., 2018, vol. 130, # 17, p. 4712 - 4716,5
  • 37
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  • [ 659729-09-6 ]
YieldReaction ConditionsOperation in experiment
49% With palladium diacetate; sodium carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 16 h; Inert atmosphere General procedure: All solvents and solutions used for this reaction were sparged with argonfor 15 minutes. In a round-bottomed flask was dissolved 4,6-dichloropyrimidine (1.5 equiv.) inTHF (1 M), under argon atmosphere. The arylboronic acid (1.0 equiv.), palladium acetate (0.02equiv., 2 molpercent), triphenylphosphine (0.04 equiv., 4 molpercent) and 1 M aqueous Na2CO3 solution(2.0 equiv.) were added and the mixture was stirred at 60 °C, overnight. After cooling to roomtemperature, the aqueous layer was extracted with Et2O and the organic layers were combined,washed with brine, dried over MgSO4, filtered and evaporated under vacuum. The crude materialwas purified by flash column chromatography to obtain the desired product.
47.2% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 120℃; for 8 h; Inert atmosphere; Sealed tube 2 g (0.011 mol) of 4-trifluoromethylbenzeneboronic acid was weighed out,4,6-dichloropyrimidine (1.60 g, 0.011 mol)Tetrakis (triphenyl palladium 0.15g with 2.5 g of anhydrous sodium carbonate was placed in a 120 mL sealed tube,A mixture of tetrahydrofen sitan 30 mL and 20 mL of deionized water was placed in a sealed tube as a solvent, and a stirrer was added and the stopper was capped.The whole device was purged with nitrogen for 3 to 4 times, placed in an oil bath and heated to 120 ° C for about 8 hours with stirring on a magnetic stirrer.After completion of the reaction, the sealing tube was cooled to room temperature, and the solution in the sealed tube was placed in a rotary vial, and the tetrahydrofuran solvent was distilled off under reduced pressure by rotary evaporator. And then extracted with ethyl acetate and water organic products 3 ~ 4 times, vacuum distillation solvent to petroleum ether: ethyl acetate 10: 1 will be steamed after the productionThe samples were separated by column chromatography and separated by separate column chromatography using dichloromethane to give about 1.28 g of a white solid in 47.2percent yield.
2.7 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 130℃; for 7 h; Example 21 2-[(4-Fluoro-benzenesulfonyl)-methyl-amino]-N-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4- ylmethyl] - acetamide A solution of 4-(trifluoromethyl)phenylboronic acid (5.0 g, 25.8 mmol), 4,6-dichloropyrimidine (3.92 g, 25.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (362 mg, 516 μιηο) and sodium carbonate (8.2 g, 77.4 mmol, Eq: 3) in a three solvent mixture of 50 mL DME, 7.5 mL ethanol and 7.5 mL water was heated at 130°C for 7 h. Upon cooling to rt, the reaction mixture was poured into saturated aqueous ammonium chloride solution and extracted with three times with ethyl acetate. The combined organic layers were washed with water and brine and dried over Na2S04. Filtration followed by removal of volatiles under reduced pressure gave a dark red solid. The mixture was purified by flash chromatography (5percent diethyl ether in hexane) to give 4-chloro-6-(4-trifluoromethyl- phenyl)-pyrimidine(2.76g) as a white solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 299 - 302
[2] Patent: CN106632488, 2017, A, . Location in patent: Paragraph 0167-0169
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3497 - 3514
[4] Patent: US2006/241296, 2006, A1, . Location in patent: Page/Page column 27
[5] Patent: WO2010/134478, 2010, A1, . Location in patent: Page/Page column 165
[6] Patent: WO2014/49047, 2014, A1, . Location in patent: Page/Page column 63
[7] Patent: WO2015/28989, 2015, A1, . Location in patent: Page/Page column 86
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Reference: [1] Patent: WO2004/46133, 2004, A1, . Location in patent: Page 40
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  • [ 457889-46-2 ]
Reference: [1] Patent: EP2725024, 2014, A1,
[2] Patent: US2014/171431, 2014, A1,
[3] Patent: US2009/215843, 2009, A1,
  • 40
  • [ 585-76-2 ]
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  • [ 199528-28-4 ]
YieldReaction ConditionsOperation in experiment
90% With palladium 10% on activated carbon; sodium carbonate In water; isopropyl alcohol at 20 - 70℃; for 4.5 h; The Suzuki coupling was carried out according to the method of Dyer et al. (Tetrahedron Letters, 2001, 42, 1765-1767). Commercially available 4-(Trifluoromethyl)phenylboronic acid (95.9g, 505 mmol) and 3-bromobenzoic acid (100.5g, 500 mmol) were suspended in 2-propanol:water (1:4, 500 mL). 10percent Pd/C (4.8g) was added. Aqueous Na2CO3 (250 mL, 20percent by wt.) was then added slowly (to control CO2 evolution) to the above mixture while vigorously stirring. The resulting mixture was stirred at room temperature for 30 min and then heated at 70C for 4 hours. The Pd/C was filtered and rinsed with 20percent aqueous Na2CO3 solution (20mL). The filtrate was acidified to pH~4 with 6N HCl, and the resulting white solid was collected by filtration and dried in vacuo. The crude product was dissolved in acetone (1.4L) then an equal volume of distilled water was added. The resulting white precipitate was collected by filtration and dried in vacuo. 120.2 g of coupled product 8.1 was acquired (yield: 90percent). MS ESI m/e: 267 (M-H). 1H NMR (500MHz) (DMSO) 13.17 (1H, s); 8.25 (1H, s); 8.03-7.99 (2H, m); 7.95 (2H, d); 7.85 (2H, d); 7.66 (1H, t). mp: 197 °C - 200 °C.
Reference: [1] Organic Process Research and Development, 2011, vol. 15, # 3, p. 570 - 580
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1267 - 1270
[3] Patent: US2006/270724, 2006, A1, . Location in patent: Page/Page column 18
[4] Patent: WO2008/30520, 2008, A1, . Location in patent: Page/Page column 107-108
[5] Patent: US2006/4012, 2006, A1, . Location in patent: Page/Page column 24
[6] Patent: WO2007/106469, 2007, A2, . Location in patent: Page/Page column 84
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Reference: [1] Patent: WO2007/125364, 2007, A1,
  • 42
  • [ 464192-28-7 ]
  • [ 128796-39-4 ]
  • [ 447406-52-2 ]
YieldReaction ConditionsOperation in experiment
21% With sodium carbonate In 1,4-dioxane; water for 20 h; Heating / reflux A mixture of 2-bromo-5-formylthioazole (525 mg, 2.73 mmol), (4-trifluoromethyl)phenylboronic acid (519 mg, 2.73 mmol), tetrakis(triphenylphosphine)palladium(0) (95 mg, 0.082 mmol) and 2 N aqueous Na2CO3 (5.5 mL, 10.94 mmol) were refluxed in dioxane (8 mL) for 20 h. It was cooled and partitioned between EtOAc and water. After separating layers, the organic phase was washed with water and brine. It was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography eluting with EtOAc/Hexane. The title compound was obtained in yellow solids (145 mg, 21percent).
Reference: [1] Patent: US2007/244094, 2007, A1, . Location in patent: Page/Page column 51-52
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Reference: [1] Organic Letters, 2016, vol. 18, # 13, p. 3082 - 3085
[2] Patent: WO2007/125364, 2007, A1, . Location in patent: Page/Page column 48
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2639 - 2648
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