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[ CAS No. 849138-20-1 ] {[proInfo.proName]}

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Chemical Structure| 849138-20-1
Chemical Structure| 849138-20-1
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Product Details of [ 849138-20-1 ]

CAS No. :849138-20-1 MDL No. :MFCD26392595
Formula : C26H32B2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 430.15 Pubchem ID :-
Synonyms :

Safety of [ 849138-20-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 849138-20-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 849138-20-1 ]

[ 849138-20-1 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 186517-01-1 ]
  • [ 73183-34-3 ]
  • [ 849138-20-1 ]
YieldReaction ConditionsOperation in experiment
99% With potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl; palladium diacetate In 1,4-dioxane at 70℃; for 20h; Inert atmosphere; Sealed tube;
78% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 85℃; for 22h; Inert atmosphere; 2,6-Dibromoanthracene and bis(pinacolato)diboron were reacted at 85 ° C for twenty-two hours using palladium acetate as a catalyst, 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl as a ligand, potassium phosphate as a base, 1,4-Dioxane is used as a solvent . The crude product was filtered through a short silica gel column, and the system of ethyl acetate and methylene chloride was applied to a short column of silica gel. The obtained filtrate was spin dried, ultrasonicated with petroleum ether for fifteen minutes, the suspension was filtered, and the obtained solid was air-dried to obtain the compound of formula 2 with a yield of 78%.
76% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 85℃; for 24h; Using 2,6-dibromoanthracene with palladium acetate as a catalyst and 2-dicyclohexylphosphine-2 ', 6'-dimethoxybiphenyl as a ligand,Potassium phosphate as base, dioxane as solvent, and Maura Borylation Reaction at 85 ° C for one day.The crude product was washed with hot petroleum ether to obtain the compound of Formula 2, with a reaction yield of 76%.
73% With potassium acetate In 1,4-dioxane at 110℃; for 15h; Inert atmosphere; 13.A To a solution of 400 mg (1.49 mmol) of 2,6-Dibromo-anthracene (13a) in 1,4- dioxane (30 mL) was added bis-pinacol borate (3.28 mmol), Pd(dppf)Cl2 (0.075 mmol) and KOAc (8.94 mmol). The reaction mixture was put under N2 atmosphere,then heated to 110 0C and allowed to stir at this temperature for about 15 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The resulting residue was purified using column chromatography on silica gel (gradient elution using petroleum etheϖEtOAc from 50: 1 to 10: 1) to provide Compound 13b (467 mg, 73% yield).
73% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 15h;
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 20 - 80℃; for 20.5h; Inert atmosphere;
48% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 16h;
48% With potassium acetate In dimethyl sulfoxide at 80℃; for 16h; 5 A nitrogen- flushed round bottom flask was charged with 2,6-dibromoanthracene (prepared as in Example 1 , 21.73 g, 64.67 mmol), bis(pinacolato)diboron (41.06 g, 161.67 mmol), potassium acetate (25.90 g, 263.85 mmol) and [1 ,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium complex with dichloromethane (1 :1 ) (1.64 g, 2.0 mmol). Dimethyl sulfoxide (DMSO, 300 ml) was then added and the mixture was bubbled with nitrogen for 15 min. After heating at 80 0C for 16 h, the reaction mixture was cooled to room temperature and poured into ice-water (600 ml). It was then extracted with methylene chloride (2x) and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation and the residue was purified several times by flash silica gel column with chloroform/hexane (1 :2 to 1 :1 to 2:1 to chloroform) as eluent to give 13.4698 g of (48%) bright yellow fine crystals, mp: >260 0C. 1H NMR (CDCI3, 500 MHz): δ 8.56 ppm (s, 2 H), 8.44 ppm (s, 2 H), 7.99-7.97 ppm (d, 2 H, J = 8.5 Hz), 7.79-7.77 ppm (d, 2 H1 J = 8.5 Hz ), δ 1.41 ppm (s, 24 H); 13C-NMR (CDCI3, 500 MHz): δ 137.7, 133.1 , 132.2, 129.5, 127.8, 127.5, 84.37, 25.33 ppm. El, MS m/z (%): 430 (100, M+). Anal. Found: C, 71.76; H, 7.32; B, 4.89
38% With potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere; AA1 A mixture of 2,6- dibromoanthracene (500 mg, 1.49 mmol), bis(pinacolato)diboron (756 mg, 2.98 mmol)and KOAc (585 mg, 5.96 mmol) in DMSO (10 mL) was degassed with N2 gas for 20 minutes. To the degassed solution was added PdCl2(dppf) (55 mg, 0.075 mmol) then the reaction was heated to 8O°C overnight. After cooling to room temperature, the reaction was poured into H2O and extracted with CH2Cl2. The organic phase was collected then washed with H2O and brine. After drying over Na2Sθ4, the organic phase was concentrated then purified by silica gel chromatography (30-100% CH2Cl2-hexanes gradient) to afford 2,6-anthracene-bis-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (241 mg, 0.56 mmol, 38% yield). 1H-NMR: 400 MHz, (DMSO-d6) δ: 8.57 (s, 2H), 8.46 (s, 2H), 8.00 (d, 2H), 7.79 (d, 2H).
With potassium acetate
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate at 80℃; 1.1 Step 1 : A Miyaura borylation reaction can be used to form (a). 2,6- dibromoanthracene can be reacted with bis(pinacolato)diboron in the presence of KOAc and PdCl2(dppf) catalyst in a solvent such as dioxane or DMSO at a temperature of 80°C. The product (a) can be isolated by conventional techniques.

Reference: [1]Huang, Ze-Ao; Chen, Chen; Yang, Xiao-Di; Fan, Xiang-Bing; Zhou, Wen; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan [Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11144 - 11147]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Technical Institute of Physics & Chemistry(in: CAS) - CN108586187, 2018, A Location in patent: Paragraph 0032; 0033
[3]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Technical Institute of Physics & Chemistry(in: CAS) - CN110272332, 2019, A Location in patent: Paragraph 0036-0037; 0052
[4]Current Patent Assignee: MERCK & CO INC - WO2010/132538, 2010, A1 Location in patent: Page/Page column 110
[5]Yu, Wensheng; Coburn, Craig A.; Yang, De-Yi; Meinke, Peter T.; Wong, Michael; Rosenblum, Stuart B.; Chen, Kevin X.; Njoroge, George F.; Chen, Lei; Dwyer, Michael P.; Jiang, Yueheng; Nair, Anilkumar G.; Selyutin, Oleg; Tong, Ling; Zeng, Qingbei; Zhong, Bin; Ji, Tao; Hu, Bin; Agrawal, Sony; Xia, Ellen; Zhai, Ying; Liu, Rong; Kong, Rong; Ingravallo, Paul; Asante-Appiah, Ernest; Nomeir, Amin; Fells, James; Kozlowski, Joseph A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3158 - 3162]
[6]Sonar, Prashant; Singh, Samarendra P.; Williams, Evan L.; Li, Yuning; Soh, Mui Siang; Dodabalapur, Ananth [Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4425 - 4435]
[7]Meng, Hong; Sun, Fangping; Goldfinger, Marc B.; Jaycox, Gary D.; Li, Zhigang; Marshall, Will J.; Blackman, Gregory S. [Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2406 - 2407]
[8]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2006/50496, 2006, A1 Location in patent: Page/Page column 40
[9]Current Patent Assignee: GILEAD SCIENCES INC - WO2010/132601, 2010, A1 Location in patent: Page/Page column 458
[10]Zhao, Yang; Yan, Lijia; Murtaza, Imran; Liang, Xiao; Meng, Hong; Huang, Wei [Organic electronics, 2017, vol. 43, p. 105 - 111]
[11]Xu, Wei; Yang, Xiao-Di; Fan, Xiang-Bing; Wang, Xin; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan [Angewandte Chemie - International Edition, 2019, vol. 58, # 12, p. 3943 - 3947][Angew. Chem., 2019, vol. 131, # 12, p. 3983 - 3987,5]
[12]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2020/33480, 2020, A1 Location in patent: Page/Page column 77
  • 2
  • [ 211737-28-9 ]
  • [ 849138-20-1 ]
  • 2-[6-(5-hexyl-thiophen-2-yl)-anthracen-2-yl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
  • bis-(5'-hexylthiophen-2'-yl)-2,6-anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; sodium carbonate In toluene at 90℃; for 72h;
  • 3
  • [ 211737-28-9 ]
  • [ 849138-20-1 ]
  • bis-(5'-hexylthiophen-2'-yl)-2,6-anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With sodium carbonate In water; toluene at 90℃; for 72h; 6 To a solution of 2,6- anthracene-bis-4',4',5',5'-tetramethyl-1 ',3',2'-dioxaborolane (prepared as in Example 5, 6.8220 g, 15.86 mmol) and 2-bromo-5-hexylthophene (8.6251 g, 34.89 mmol) dissolved in toluene (240 ml) was added sodium carbonate (8.48 g, 80 mmol) dissolved in water (40 ml) followed by th e addition of phase-transfer agent Aliquat 336 (3.2 g, 8.0 mmol). The mixture was bubbled with nitrogen for 15 min. Then, tetrakis(triphenylphosphine)palladium(0) (368 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into methanol (600 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), water, methanol, then with acetone (3x) to remove the starting material and mono-substituted by¬ product. The crude product was purified by sublimation (2Z0 °C/60 mmTorr) in a 3-zone furnace, followed by recrystallization from xylenes to give 4.2802 g (53%) of bright yellow product. 1H NMR (p-d ichlorobenzene- d4, 500 MHz): δ 8.15 ppm (s, 2 H), 8.01 ppm (s, 2 H), 7.82-7.80 ppm (d, 2 H, J = 8.5 Hz), 7.61-7.59 ppm (d, 2 H, J = 8.5 Hz ), 7.19 ppm (d, 2 H, J = 3.45 Hz), 7.02 ppm (d, 2 H, J = 3.45 Hz), 6.71 ppm (s, 2 H ), 2.80-2.77 ppm (t, 2 H, J = 8.6 Hz), 1.70 ppm (m, 2 H), 1.32 ppm (m, 6 H), 0.89 ppm (t, 3 H, J = 7.5 Hz);; 13C-NMR (CDCI3, 500 MHz): δ 146.6, 142.7, 132.8, 132.4, 132.2, 130.2, 129.3, 126.8, 125.9, 125.1 , 124.0, 32.36, 32.28, 31.11 , 29.64, 23.33, 14.63 ppm. El, MS m/z (%): 510 (100, M+); HRMS found: 510.241463. Compounds 9 - 15 were synthesized in a similar manner as that described for the synthesis of DHTAnt.
  • 4
  • [ 1007882-59-8 ]
  • [ 849138-20-1 ]
  • [ 1240886-16-1 ]
YieldReaction ConditionsOperation in experiment
61% With sodium carbonate In tetrahydrofuran; water for 15h; Inert atmosphere; Reflux; 13.B A suspension of Compound 13b (467 mg, 1.09 mmol, prepared as described in theJournal of the American Chemical Society, 127: 8; 2005; 2406 - 2407), (S)-tert-butyl 2-(5-bromo-lH-imidazol-2-yl)pyrrolidine-l-carboxylate (2.18 mmol), Pd(dppf)2Cl2 (0.109 mol), Na2CO3 (6.52 mmol) in THF/H2O (10:1, 20 mL) was put under N2 atmosphere, then heated to reflux and allowed to stir at this temperature for about 15 hours. The reaction mixture was cooled to room temperature and filtered and the filtrate was washed with water (20 mL) and extracted with EtOAc (50 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was purified using column chromatography (Gradient Pet ether: Ethyl Acetate from 10: 1 to 1:9) to provide Compound 13c (706 mg, 61% yield). MS (ESI) m/e (M+H)+: 649
61% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water for 15h; Reflux;
  • 5
  • [ 1352718-88-7 ]
  • [ 849138-20-1 ]
  • C38H44N6O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; toluene; at 80.0℃;Inert atmosphere; A solution of 2,6-anthracene-bis-4,4,5,5- tetramethyl-l ,3,2-dioxaborolane (241 mg, 0.56 mmol), 2-(5-bromo-1H-imidazol-2-yl)- pyrrolidine-1-carboxylic acid tert-butyl ester (531 mg, 1.68 mmol) and aq K2Ctheta3 (1.12 mL of a 2M solution, 2.24 mmol) in toluene (6 mL) and DMF (1 mL) was degassed with N2 gas for 20 minutes. To the degassed solution was added Pd(PPh3)4 (32 mg, 0.028 mmol) and PdCl2(dppf) (21 mg, 0.028 mmol) then the reaction was heated to 80C overnight. After cooling to room temperature, the reaction was concentrated. The crude material was diluted with EtOAc then washed with saturated NaHCO3. The aqueous phase was back-extracted two times then the organic layers were combined, dried over Na2SO4, and concentrated. The crude product was purified by reverse phase preparative HPLC (20-80% MeCN-H2O; 0.1% formic acid modifier) to afford l-[2-(5-{6-[2-(l-1-/err-butoxycarbonyl-py?-olidin-2-yl)-3H-imidazol-4-yl]-anthracen- 2-yl}-1H-imidazol-2-yl)-pyrrolidin-1-yl]-ethanone (117 mg, 0.18 mmol, 32% yield). LCMS- ESI+: CaIcd. for C38H45N6O4: 649.4 (M+H+); Found: 648.9 (M+H+).
  • 6
  • CH2Cl2-hexanes [ No CAS ]
  • bis(pinacolato)diboron [ No CAS ]
  • PdCl2dppf2 [ No CAS ]
  • [ 186517-01-1 ]
  • [ 849138-20-1 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In dimethyl sulfoxide 13 Preparation of Compound 13 Example 13 Preparation of Compound 13 2,6-Anthracene-bis-4,4,5,5-tetramethyl-1,3,2-dioxaborolane: A mixture of 2,6-dibromoanthracene (500 mg, 1.49 mmol), bis(pinacolato)diboron (756 mg, 2.98 mmol) and KOAc (585 mg, 5.96 mmol) in DMSO (10 mL) was degassed with N2 gas for 20 minutes. To the degassed solution was added PdCl2dppf2 (55 mg, 0.075 mmol) then the reaction was heated to 80° C. overnight. After cooling to room temperature, the reaction was poured into H2O and extracted with CH2Cl2. The organic phase was collected then washed with H2O and brine. After drying over Na2SO4, the organic phase was concentrated then purified by silica gel chromatography (30-100% CH2Cl2-hexanes gradient) to afford 2,6-anthracene-bis-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (241 mg, 0.56 mmol, 38% yield). 1H-NMR: 400 MHz, (DMSO-d6) δ: 8.57 (s, 2H), 8.46 (s, 2H), 8.00 (d, 2H), 7.79 (d, 2H).
  • 7
  • [ 186517-01-1 ]
  • [ 25015-63-8 ]
  • [ 849138-20-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene
  • 8
  • [ 26608-06-0 ]
  • [ 849138-20-1 ]
  • 2,6-bis(dibenzo[b,d]furan-3-yl)anthracene [ No CAS ]
  • 9
  • [ 393-36-2 ]
  • [ 849138-20-1 ]
  • 2,6-bis(4-amino-2-trifluoromethylphenyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 85℃; for 72h;Inert atmosphere; A mixture of 2,6-bis-Bpin anthracene 1 (14.5 g, 33.71 mmole), 4- bromo-3-(trifluoromethyl)aniline 2 (24.27 g, 101 .13 mmole), Pd(PPh3)4 (3.9 g, 3.37 mmole) and potassium carbonate (23.29 g, 169 mmole) in toluene (400 ml), ethanol (200 ml) and water (80 ml) was degassed and stirred with heating at 85C under nitrogen atmosphere for 3 days. Precipitated from reaction mixture product 3 (9.7 g) was collected by hot filtration. Filtrate cooled down, precipitate collected by filtration to give 3.2 g of the product with lower purity. 1H-NMR (DMSO-d6, 500 MHz): 5.69 (s, 4H), (0641) 6.88 (dd, 2H, J1 = 2 Hz, J2 = 8 Hz), 7.03 (d, 2H, J = 2 Hz), 7.18 (d, 2H, J = 8 Hz), 7.40 (d, 2H, J = 9 Hz), 7.92 (s, 2H), 8.05 (d, 2H, J = 9 Hz), 8.58 (s, 2H).
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