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Chemical Structure| 99768-12-4
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Product Citations

Campbell, Allea ; Alsudairy, Ziad ; Dun, Chaochao , et al. DOI:

Abstract: Covalent organic framework (COF)-supported palladium catalysts have garnered enormous attention for cross-coupling reactions. However, the limited linkage types in COF hosts and their suboptimal catalytic performance have hindered their widespread implementation. Herein, we present the first study immobilizing palladium acetate onto a dioxin-linked COF (Pd/COF-318) through a facile solution impregnation approach. By virtue of its permanent porosity, accessible Pd sites arranged in periodic skeletons, and framework robustness, the resultant Pd/COF-318 exhibits exceptionally high activity and broad substrate scope for the Suzuki-Miyaura coupling reaction between aryl bromides and arylboronic acids at room temperature within an hour, rendering it among the most effective Pd/COF catalysts for Suzuki-Miyaura coupling reactions to date. Moreover, Pd/COF-318 demonstrates excellent recyclability, retaining high activity over five cycles without significant deactivation. The leaching test confirms the heterogeneity of the catalyst. This work uncovers the vast potential of dioxin-linked COFs as catalyst supports for highly active, selective, and durable organometallic catalysis.

Keywords: covalent organic framework (COF) ; dioxin-linked COF ; Pd(II) immobilization ; Suzuki-Miyaura coupling

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Product Details of [ 99768-12-4 ]

CAS No. :99768-12-4 MDL No. :MFCD01632203
Formula : C8H9BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :PQCXFUXRTRESBD-UHFFFAOYSA-N
M.W : 179.97 Pubchem ID :2734369
Synonyms :
4-Methoxycarbonylbenzeneboronic acid
Chemical Name :(4-(Methoxycarbonyl)phenyl)boronic acid

Calculated chemistry of [ 99768-12-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 47.55
TPSA : 66.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.68
Log Po/w (WLOGP) : -0.85
Log Po/w (MLOGP) : 0.2
Log Po/w (SILICOS-IT) : -0.87
Consensus Log Po/w : -0.17

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.53
Solubility : 5.34 mg/ml ; 0.0297 mol/l
Class : Very soluble
Log S (Ali) : -1.66
Solubility : 3.95 mg/ml ; 0.0219 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.36
Solubility : 7.8 mg/ml ; 0.0434 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 99768-12-4 ]

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 [ 99768-12-4 ]

* 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 [ 99768-12-4 ]
  • Downstream synthetic route of [ 99768-12-4 ]

[ 99768-12-4 ] Synthesis Path-Upstream   1~48

  • 1
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  • [ 26000-33-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 14, # 1, p. 122 - 130
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 10, p. 2701 - 2705[3] Angew. Chem., 2014, vol. 53, # 10, p. 2739 - 2743,5
  • 2
  • [ 99768-12-4 ]
  • [ 26000-33-9 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 11, p. 2892 - 2895
[2] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803
[3] Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11278 - 11282
  • 3
  • [ 615-36-1 ]
  • [ 99768-12-4 ]
  • [ 26000-33-9 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 6, p. 1597 - 1600
  • 4
  • [ 99768-12-4 ]
  • [ 29886-62-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7151 - 7154
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2087 - 2103
  • 5
  • [ 1899-24-7 ]
  • [ 99768-12-4 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
81% With potassium fluoride; tri-tert-butyl phosphine In 1,4-dioxane; hexane at 65 - 70℃; for 4 h; A solution of 5-bromofuraldehyde (2.43 g, 13.9 mmoles), 4-(methoxycarbonyl)phenylboronic acid (2.50 g, 13.9 mmoles), tris(dibenzylideneacetone)palladium (0) (192 mg, 0.2 mmoles) and potassium fluoride (2.42 g, 41.7 mmoles) in 1,4-dioxane (100 ml) was added with a solution of tri-toert-butylphosphine in hexane (10percent by weight, 101 mg, 0.5 mmoles). After heating at 65-70°C for 4 hours, the mixture was cooled to room temperature and treated with methylene chloride (150 ml). After stirring for 10 minutes, the mixture was filtered through Celite and the filtrate was EPO <DP n="13"/>concentrated under reduced pressure. The residue was purified by flash silica gel chromatography eluting with an ethyl acetate-hexane mixture (1 : 1) to give 4-(5-formyl-furan-2-yl)-benzoic acid methyl ester (2.6 g, 81percent yield).1H NMR (300 MHz, CDCl3): δ 9.70 (s, IH), 8.10 (d, 2H), 7.90 (d, 2H), 7.35 (d, IH), 6.95 (d, IH), 3.98 (s, 3H).
78% With palladium diacetate; sodium carbonate In water; acetone at 20℃; for 0.416667 h; To a solution of sodium carbonate (588.2 mg, 5.55 mmol) in H2O /acetone (278 mL/ 555 mL) was added 5-bromo-2-furaldehyde (1.9 g, 11 mmol), p-(methoxycarbonyl)phenyl boronic acid (2.0 g, 11 mmol) followed by palladium acetate(24.9 mg, 0.111 mmol) in acetone (278 ml). The reaction mixture was stirred at room temperature for 25 min. The reactionwas quenched by diluting with EtOAc (855 mL) and the organic layer was washed with 1 M HCl (500 mL) twice andwith brine (500 mL) once. The organic layer was dried over Na2SO4 and filtered with silica gel, which was concentratedin vacuo. The residue was purified by flash column chromatography (CH2Cl2/hexane = 9/ 1) to give compound 9 as whitesolid (2.0 g, 8.7 mmol, 78percent)
73% With Pd(N,N-dimethyl-β-alaninate)2; sodium carbonate In ethanol; water at 120℃; for 0.166667 h; Microwave irradiation; Sealed tube General procedure: To a solution of the appropriate bromo-substituted heterocyclic aldehydes 17a (1.0 mmol) in EtOH/H2O 5:3 (tot 12 mL) in a 35 mL CEM microwave vessel, the correspondent boronic acids 18c-d (1.2 mmol), Na2CO3 2M (2.0 mmol) and Pd(N,N-Dimethyl β-alaninate)2 (5 molpercent) were added. The vessel was capped and placed in a microwave reactor and the reaction carried out with the following method in dynamic mode: 120° C, 10 min, 50W, with high stirring. After completion the vessel was allowed to cool to room temperature and the mixture was extracted with EtOAc (3 X 10 mL). The organic phase was collected, dried over anhydrous Na2SO4, and the solvent evaporated under vacuum. The crude product (containing a small portion of the ethyl ester as a transesterification product) was then purified via silica gel column chromatography (petroleum ether/EtOAc elution gradient from a 90/10 ratio to a 80/20 ratio) to obtain the pure compounds (yield 40-60percent) (Scheme 1).
Reference: [1] Patent: WO2006/66846, 2006, A1, . Location in patent: Page/Page column 11; 12
[2] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 9, p. 1562 - 1565
[3] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 63 - 70
  • 6
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  • [ 13716-12-6 ]
  • [ 99768-12-4 ]
  • [ 53355-29-6 ]
YieldReaction ConditionsOperation in experiment
81% With potassium fluoride In hexane; dichloromethane A.
4-(5-Formyl-furan-2-yl)-benzoic Acid Methyl Ester
To a solution of 5-bromofuraldehyde (2.43 g, 13.9 mmol), 4-(methoxycarbonyl)phenyl boronic acid (2.50 g, 13.9 mmol), tris(dibenzylideneacetone)dipalladium(0) (192 mg, 0.21 mmol) and potassium fluoride (2.42 g, 41.7 mmol) in 1,4-doxane (100 ml) was added a solution of tri-t-butylphosphine in hexane (10 weight percent, 1.01 g, 0.5 mmol).
After heating at 65-70° C. for 4 hours, the mixture was cooled to room temperature and treated with dichloromethane (150 ml).
After stirring for 10 minutes, the mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure.
The residue was purified by flash chromatography on silica gel eluding with ethyl acetate-hexane (1:1) to provide 4-(5-formyl-furan-2-yl)-benzoic acid methyl ester (2.6 g, 81percent yield).
Reference: [1] Patent: US2004/2526, 2004, A1,
  • 7
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  • [ 59662-46-3 ]
Reference: [1] Patent: WO2013/123456, 2013, A1,
[2] Patent: WO2017/84629, 2017, A1,
[3] Patent: WO2017/84630, 2017, A1,
  • 8
  • [ 107-14-2 ]
  • [ 99768-12-4 ]
  • [ 76469-88-0 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
[2] Advanced Synthesis and Catalysis, 2015, vol. 357, # 12, p. 2721 - 2727
  • 9
  • [ 6011-14-9 ]
  • [ 99768-12-4 ]
  • [ 76469-88-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 10
  • [ 626-39-1 ]
  • [ 99768-12-4 ]
  • [ 50446-44-1 ]
Reference: [1] Patent: US2015/152123, 2015, A1,
[2] Patent: EP2876112, 2015, A1,
  • 11
  • [ 1363789-11-0 ]
  • [ 99768-12-4 ]
  • [ 89901-03-1 ]
YieldReaction ConditionsOperation in experiment
36% With chloro[tris(para-trifluoromethylphenyl)phosphine]gold (I); cesium fluoride In methanol at 20℃; for 15 h; Irradiation; Inert atmosphere In a dried Pyrex screwtop reaction tube (4CF3C6H4)3PAuC (0.01 mmo, 10 mo percent)and (4(methoxycarbony)pheny)boronic acid (0.1 mmo, 1.0 equiv.) were dissoved in0.5 mL MeCH, After adding CsF (0.2 mmol, 2.0 equiv.) 4bromobenzenediazoniumbis((trWuoromethy)sufony)amide (0.4 mmoL 0.4 equiv,) the reaction mixture was de gassed under argon by sparging for 51 0 mm. The tube was irradiated with 29 W bue LEDs for 15 hours. The crude mixture was subjected to GCMS analysis, product 3o was detected, The product was purified by pTLC (SiC2, PE/EA, 5:1) to give 10.5 mg of 30 (0.04 mmol, 36percent). This shows, that adding an external fluoride source the reactionsproceeds and the desired product can be formed,
Reference: [1] Patent: WO2018/114914, 2018, A1, . Location in patent: Page/Page column 45
  • 12
  • [ 589-87-7 ]
  • [ 99768-12-4 ]
  • [ 89901-03-1 ]
Reference: [1] Journal of Materials Chemistry A, 2015, vol. 3, # 46, p. 23493 - 23500
  • 13
  • [ 106-40-1 ]
  • [ 99768-12-4 ]
  • [ 89901-03-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 9, p. 1522 - 1528
  • 14
  • [ 99768-12-4 ]
  • [ 69812-51-7 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641
  • 15
  • [ 288-32-4 ]
  • [ 99768-12-4 ]
  • [ 101184-08-1 ]
YieldReaction ConditionsOperation in experiment
84% With CuI-USY zeolite In methanol at 65℃; for 17 h; General procedure: In a 10-mL round-bottom flask were successively added CuI-USY (ca. 15 mg, 10 molpercent of copper species), the nucleophile (0.75 mmol, 1.5 equiv), the boronic acid (0.5 mmol, 1.0 equiv), and MeOH (3.0 mL). The mixture was refluxed under air for 17 h and analyzed by LCMS. After cooling to r.t., the solvent was removed and the desired compound was isolated by purification on a short pad of silica gel (cyclohexane/EtOAc mixture).
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 6, p. 1223 - 1230
[2] Synthetic Communications, 2012, vol. 42, # 17, p. 2595 - 2605
  • 16
  • [ 1120-87-2 ]
  • [ 99768-12-4 ]
  • [ 106047-17-0 ]
YieldReaction ConditionsOperation in experiment
86.8% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 90℃; for 10 h; Inert atmosphere Step A:
Under nitrogen atmosphere, a mixture of 4-bromopyridine (3.0 g, 19.0 mmol), (4-(methoxycarbonyl)phenyl)boric acid (2.63 g, 14.6 mmol), Pd(PPh3)2Cl2(0.35 g, 0.5 mmol) and sodium carbonate (6.91 g, 65.2 mmol) in 1,2-dimethoxylethane (40 mL) was heated to 90°C and stirred for 10 h.
The resultant mixture was concentrated under reduced pressure and the residue was purified with silica gel column chromatography (eluent: petroleum ether/ethyl acetate=6/1-2/1) to give methyl 4-(pyridine-4-yl)benzoate (2.7 g, yield: 86.8percent) as white solid.
MS(ESI)m/z:214[M+H+].
86.8% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 90℃; for 10 h; Inert atmosphere A solution of 4-bromopyridine (3.0 g, 19.0 mmol), (4- (methoxycarbonyl) phenyl) boronic acid (2.63 g, 14.6 mmol), Pd (PPh3) 2Cl2 (0.35 g, 0.5 mmol ) And sodium carbonate (6.91 g, 65.2 mmol)1,2-dimethoxyethane (40 ml) was heated to 90 ° C under a nitrogen atmosphere and stirred for 10 hours.The resulting mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent:Petroleum ether / ethyl acetate = 6/1 to 2/1)4- (pyridin-4-yl) benzoate(2.7 g, yield: 86.8percent) as a white solid.
26.4% With sodium carbonate In 1,4-dioxane; water 2.45a.methyl 4-pyridin-4-yl-benzoate
3.0 g (15 mmol) of 4-bromo-pyridine is dissolved in 50 mL dioxane and 15 mL 2M sodium carbonate solution. 2.7 g (15 mmol) of 4-methoxycarbonylphenyl-boric acid and 1.73 g (2 mmol) of tetrakis-(triphenylphosphine)-palladium are added successively and the reaction is refluxed for 6 h.
The hot reaction solution is suction filtered through a glass fibre filter.
The solvent is eliminated using the rotary evaporator and the purification is carried out by column chromatography on silica gel (dichloromethane/methanol 9:1).
Yield: 845 mg (26.4percent of theory);
C13H11NO2 (M=213.238);
calc.: molar peak (M+H)+: 214 fnd.: molar peak (M+H)+: 214;
Retention time HPLC: 4.1 min (method A).
Reference: [1] Patent: EP3190113, 2017, A1, . Location in patent: Paragraph 0101
[2] Patent: TWI558709, 2016, B, . Location in patent: Page/Page column 50; 51
[3] Patent: US2004/242572, 2004, A1, . Location in patent: Page/Page column 73
  • 17
  • [ 626-64-2 ]
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  • [ 106047-17-0 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 14, p. 4038 - 4042
  • 18
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  • [ 171623-29-3 ]
Reference: [1] Patent: WO2014/144836, 2014, A2,
  • 19
  • [ 287-92-3 ]
  • [ 99768-12-4 ]
  • [ 160598-47-0 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 4, p. 998 - 1001
  • 20
  • [ 5419-55-6 ]
  • [ 619-42-1 ]
  • [ 99768-12-4 ]
YieldReaction ConditionsOperation in experiment
95.5% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-bromobenzoate (20.2 g, 77.2 mmol) was dissolved in dry THF (200.0 mL)Triisopropyl borate (18.9 g, 100.3 mmol) was added,Cool to -78 ° C,N-Butyllithium (6.8 g, 96.5 mmol) was added dropwise,Maintain the reaction temperature 0.5h.The reaction is completed,Saturated aqueous ammonium chloride solution was quenched,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL × 3), the organic phases were combined,Saturated brine (60 mL × 1), dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure, the residue was beaten with n-hexane,The filtrate was filtered to give 4-methoxycarbonyl phenylboronic acid 13.3g, a yield of 95.5percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0063; 0064
  • 21
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YieldReaction ConditionsOperation in experiment
94.8% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-iodobenzoate (20.1 g, 76.7 mmol) was dissolved in dry THF (200.0 mL)Triisopropyl borate (18.0 g, 95.9 mmol) was added,Cool to -78 ° C,N-Butyllithium (6.1 g, 95.9 mmol) was added dropwise,Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL x 3)The combined organic phase,Saturated brine (60 mL × 1)Dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure,The residue was beaten with n-hexane, and filtered to obtain 13.1 g of 4-methoxycarbonylphenylboronic acid,Yield 94.8percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0023; 0024; 0079; 0080
  • 22
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  • [ 619-44-3 ]
  • [ 99768-12-4 ]
YieldReaction ConditionsOperation in experiment
91% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-iodobenzoate (20.4 g, 77.8 mmol) was dissolved in dry THF (200.0 mL)Tri-n-butyl borate (21.5 g, 93.4 mmol) was added,Cool to -78 ° C,N-Butyllithium (5.5 g, 85.6 mmol) was added dropwise,Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL x 3)The combined organic phases were washed with saturated brine (60 mL × 1)Dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure,The residue was beaten with n-hexane,Filtered to give 4-methoxycarbonyl phenylboronic acid 12.7g, the yield was 91.0percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0039; 0040
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YieldReaction ConditionsOperation in experiment
94.5% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-iodobenzoate (20.3 g, 77.4 mmol) was dissolved in dry THF (200.0 mL)Trimethyl borate (16.1 g, 154.8 mmol) was added,The temperature was lowered to -78 ° C and n-butyllithium (7.4 g, 116.1 mmol) was added dropwise.Maintain the reaction temperature 0.5h.The reaction was completed, quenched with saturated aqueous ammonium chloride solution,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL × 3), the organic phases were combined,Saturated brine (60 mL × 1), dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure, the residue was beaten with n-hexane,The filtrate was filtered to give 4-methoxycarbonyl phenylboronic acid 13.2g, a yield of 94.5percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0047; 0048
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[2] Patent: US2008/76762, 2008, A1, . Location in patent: Page/Page column 44-45
[3] Journal of the American Chemical Society, 2007, vol. 129, # 36, p. 11265 - 11278
[4] Journal of the American Chemical Society, 2007, vol. 129, # 36, p. 11265 - 11278
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 11, p. 3606 - 3610[6] Angew. Chem., 2016, vol. 128, # 11, p. 3670 - 3674,5
[7] Journal of the American Chemical Society, 2009, vol. 131, # 47, p. 17500 - 17521
[8] Inorganic Chemistry, 2013, vol. 52, # 19, p. 10732 - 10734
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[2] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
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Reference: [1] Patent: CN106565761, 2017, A,
[2] Patent: CN106565761, 2017, A,
[3] Patent: CN106565761, 2017, A,
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 11, p. 3606 - 3610[2] Angew. Chem., 2016, vol. 128, # 11, p. 3670 - 3674,5
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  • [ 201530-41-8 ]
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  • 41
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  • [ 199678-12-1 ]
Reference: [1] Patent: US2016/237043, 2016, A1,
  • 42
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  • [ 99768-12-4 ]
  • [ 393522-78-6 ]
YieldReaction ConditionsOperation in experiment
24% With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 70℃; To a solution of (4-bromophenyl)methanol (500 mg, 2.94 mmol) and [4-(methoxycarbonyl) phenyl]boronic acid (550 mg, 3.53 mmol) in DMF (20 mL) was added Pd(OAc)2 (200 mg, 735 μmol) and Na2CO3 (3 g in 20 mL H2O).
The reaction mixture was allowed to stir at 70 °C.
After 48 h, an extraction with EtOAc was performed; the organic layers were combined and washed with brine, dried over MgSO4, filtrated and concentrated in vacuo.
Column chromatography (EtOAc/Hept 1:4) yielded the product (170 mg, 24percent) as white crystals. RF = 0.3 (EtOAc/Hept 1:1).
1H NMR (400 MHz, CDCl3) δ 8.15-8.06 (m, 2H), 7.70-7.58 (m, 4H), 7.52-7.43 (m, 2H), 4.77 (d, J = 3.1 Hz, 2H), 4.07-3.67 (m, 3H), 1.75 (br s, 1H, OH) ppm. FTIR = 3305, 3032, 1718, 1604, 1432, 1399, 1286, 1271, 1220, 1111, 765 cm-1. HRMS (EI) calcd for C15H14O3 (M)+ 242.0942, found 242.0919.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 20, p. 5593 - 5603
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  • [ 128-63-2 ]
  • [ 99768-12-4 ]
  • [ 933047-52-0 ]
Reference: [1] Patent: US2016/46738, 2016, A1,
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  • [ 926304-76-9 ]
YieldReaction ConditionsOperation in experiment
48% With oxygen; caesium carbonate In 1,2-dimethoxyethane; water at 20℃; for 10 h; Examples 64-77 (Table 1) and Examples 78-83 (Table 2) show preparation of representative compounds by a procedure similar to that of Scheme 4, but with the inclusion of water (0.8percent) in the reaction mixture:
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 41, p. 5733 - 5736
[2] Organic Letters, 2009, vol. 11, # 12, p. 2511 - 2514
[3] Patent: US2009/291971, 2009, A1, . Location in patent: Page/Page column 34
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  • [ 51760-21-5 ]
  • [ 99768-12-4 ]
  • [ 677010-20-7 ]
Reference: [1] Patent: US2015/152123, 2015, A1,
[2] Patent: EP2876112, 2015, A1,
  • 46
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  • [ 936130-82-4 ]
Reference: [1] Patent: TWI558709, 2016, B,
  • 47
  • [ 1120-87-2 ]
  • [ 99768-12-4 ]
  • [ 936130-82-4 ]
Reference: [1] Patent: EP3190113, 2017, A1,
  • 48
  • [ 99768-12-4 ]
  • [ 1056634-68-4 ]
Reference: [1] Patent: EP2949647, 2015, A1,
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