* 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.
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
2
[ 64-17-5 ]
[ 1802-30-8 ]
[ 1762-46-5 ]
Yield
Reaction Conditions
Operation in experiment
77%
at 0℃; for 24 h; Reflux
Diethyl 2,2'-bipyridine-5,5'-dicarboxylate Procedure: Bipy55'DC (200 mg, 0.82 mmoles) and EtOH (13 mL) were added to a dried flask and stirred on ice. Thionyl chloride (1.3 mL) was added dropwise on ice, after which the flask was fitted with a reflux condenser and heated at reflux. After 24 hr, the reaction was cooled on ice and quenched by the dropwise addition of saturated Na2CO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (4*20 mL) and the combined organics were dried over Na2SO4(s), and concentrated under reduced pressure. The crude product was then purified by chromatography on silica (3percent acetone in 1:1 DCM/hexanes) to afford the title compound (190 mg, 77percent) as a white solid. 1H NMR (500 MHz, CDCl3) δ 9.32 (dd, J=0.5, 2.0 Hz, 1H), 8.59 (dd, J=0.5, 8.5 Hz, 1H), 8.46 (dd, J=2.0, 8.5 Hz, 1H), 4.47 (q, J=7.5 Hz, 2H), 1.46 (t, J=7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 165.2, 158.3, 150.6, 138.1, 126.6, 121.3, 61.6, 14.3; HRMS (ESI) m/z 301.1193 [calc'd for C16H17N2O4 (M+H)+ 301.1183].
Reference：
[1] Inorganic Chemistry, 2017, vol. 56, # 3, p. 1366 - 1374
[2] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[3] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885
[4] Chemical Communications, 2016, vol. 52, # 48, p. 7600 - 7603
[5] Journal of the American Chemical Society, 2017, vol. 139, # 49, p. 17747 - 17750
[6] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2457 - 2465
[7] Chemistry - A European Journal, 2018,
[8] Patent: US2016/280701, 2016, A1, . Location in patent: Paragraph 0300; 0301; 0302
[9] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[10] Journal of Molecular Catalysis A: Chemical, 2010, vol. 331, # 1-2, p. 117 - 124
[11] European Journal of Inorganic Chemistry, 1999, # 9, p. 1507 - 1521
[12] Chemical Communications, 2009, # 41, p. 6237 - 6239
[13] Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 191,193
[14] Journal of the American Chemical Society, 1982, vol. 104, # 26, p. 7519 - 7526
[15] Dalton Transactions, 2008, # 28, p. 3701 - 3708
[16] Physical Chemistry Chemical Physics, 2014, vol. 16, # 28, p. 14874 - 14881
[17] Patent: CN106496113, 2017, A, . Location in patent: Paragraph 0059; 0060; 0066; 0067; 0073; 0074
3
[ 151917-39-4 ]
[ 1762-46-5 ]
Yield
Reaction Conditions
Operation in experiment
84%
With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide; isopropyl alcohol at 100℃; for 6 h;
General procedure: A 100 mL round bottom flask was equipped with a magnetic stir bar and charged with the appropriate aryl iodide (1 equiv), K2CO3 (1.5 equiv), iPrOH (2 equiv), Pd(OAc)2 (5 mol percent), and a sufficient volume of DMF to make a 0.35 M solution. The reaction mixture was placed under nitrogen and heated to 100 C for 2–5 h until the starting material was consumed as judged by TLC analysis. The reaction mixture was cooled to room temperature and brine (40 mL) was added. The resulting mixture was transferred to a separatory funnel and extracted with EtOAc (3 × 75 mL). The organic layers were combined, washed with brine (1 × 75 mL), dried with Na2SO4, and the solvent was removed in vacuo to afford the crude product as a solid. The crude solid was purified by flash column chromatography or by recrystallization.
Reference：
[1] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 61 - 65
4
[ 614-18-6 ]
[ 1762-46-5 ]
Reference：
[1] Journal of Organic Chemistry, 1997, vol. 62, # 9, p. 3013 - 3014
[2] Journal of the American Chemical Society, 1987, vol. 109, # 22, p. 6619 - 6626
[3] Angewandte Chemie, 1986, vol. 98, # 12, p. 1119 - 1121
[4] Dalton Transactions, 2011, vol. 40, # 21, p. 5706 - 5710
[5] Journal of the Chemical Society, 1956, p. 616,619
[6] Journal of the Chemical Society, 1961, p. 1347,1349
5
[ 1762-34-1 ]
[ 1762-46-5 ]
Reference：
[1] European Journal of Inorganic Chemistry, 1999, # 9, p. 1507 - 1521
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
[3] Journal of the American Chemical Society, 1982, vol. 104, # 26, p. 7519 - 7526
[4] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[5] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[6] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
[7] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885
[8] Chemistry - A European Journal, 2018,
6
[ 1802-30-8 ]
[ 1762-46-5 ]
Reference：
[1] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
7
[ 64-17-5 ]
[ 1802-30-8 ]
[ 1762-46-5 ]
[ 105501-69-7 ]
Reference：
[1] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3853 - 3858
8
[ 108-99-6 ]
[ 1762-46-5 ]
Reference：
[1] Journal of the American Chemical Society, 1982, vol. 104, # 26, p. 7519 - 7526
Diethyl 2,2'-bipyridine-5,5'-dicarboxylate Procedure: Bipy55'DC (200 mg, 0.82 mmoles) and EtOH (13 mL) were added to a dried flask and stirred on ice. Thionyl chloride (1.3 mL) was added dropwise on ice, after which the flask was fitted with a reflux condenser and heated at reflux. After 24 hr, the reaction was cooled on ice and quenched by the dropwise addition of saturated Na2CO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (4*20 mL) and the combined organics were dried over Na2SO4(s), and concentrated under reduced pressure. The crude product was then purified by chromatography on silica (3% acetone in 1:1 DCM/hexanes) to afford the title compound (190 mg, 77%) as a white solid. 1H NMR (500 MHz, CDCl3) delta 9.32 (dd, J=0.5, 2.0 Hz, 1H), 8.59 (dd, J=0.5, 8.5 Hz, 1H), 8.46 (dd, J=2.0, 8.5 Hz, 1H), 4.47 (q, J=7.5 Hz, 2H), 1.46 (t, J=7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) delta 165.2, 158.3, 150.6, 138.1, 126.6, 121.3, 61.6, 14.3; HRMS (ESI) m/z 301.1193 [calc'd for C16H17N2O4 (M+H)+ 301.1183].
With sulfuric acid; at 80℃; for 5h;
4,4-Dicarboxylic acid-2,2-bipyridine (4.88 g) was added to 27.60 g of ethanol, 1.84 g of concentrated sulfuric acid (98%) was added,After reacting for 5 hours at 80 degrees Celsius, 0.75 parts by mass of the solvent was distilled off by distillation under reduced pressure and treated with 10.00 g of water and 74.00 g of bisMethylene chloride was subjected to extraction and separation, and the solvent was separated and evaporated twice to give 5.70 g of the crude product in a yield of 95%.
With hydrazine hydrate; In methanol; at 35℃; for 4h;
The crude product obtained according to step (1) was reacted with ethyl 4,4-dicarboxylate-2,2-dipyridine, and 3.00 g of the product was dissolved in23.70 g of methanol was added with 24.00 g of hydrazine hydrate (50percent), mass ratio: 1.00: 8.00, stirred vigorously at 350 rpm at room temperature with white insolubles, and then heated to 35 ° C. for 4 hours to prepare Crude product 2.61 g Yield 96percent
With palladium diacetate; potassium carbonate; In N,N-dimethyl-formamide; isopropyl alcohol; at 100℃; for 6h;
General procedure: A 100 mL round bottom flask was equipped with a magnetic stir bar and charged with the appropriate aryl iodide (1 equiv), K2CO3 (1.5 equiv), iPrOH (2 equiv), Pd(OAc)2 (5 mol percent), and a sufficient volume of DMF to make a 0.35 M solution. The reaction mixture was placed under nitrogen and heated to 100 C for 2?5 h until the starting material was consumed as judged by TLC analysis. The reaction mixture was cooled to room temperature and brine (40 mL) was added. The resulting mixture was transferred to a separatory funnel and extracted with EtOAc (3 × 75 mL). The organic layers were combined, washed with brine (1 × 75 mL), dried with Na2SO4, and the solvent was removed in vacuo to afford the crude product as a solid. The crude solid was purified by flash column chromatography or by recrystallization.
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