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Chemical Structure| 18471-73-3
Chemical Structure| 18471-73-3
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Product Details of [ 18471-73-3 ]

CAS No. :18471-73-3 MDL No. :MFCD04116305
Formula : C11H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :BXYRAPNURYRQSP-UHFFFAOYSA-N
M.W :170.21 Pubchem ID :459518
Synonyms :

Safety of [ 18471-73-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 18471-73-3 ]

* 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 [ 18471-73-3 ]
  • Downstream synthetic route of [ 18471-73-3 ]

[ 18471-73-3 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 4282-47-7 ]
  • [ 18471-73-3 ]
YieldReaction ConditionsOperation in experiment
87% With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 18 h; A solution of compound52(0.2 g, 1.03 mmol) in methanol (10 mL) was treated with 10percent palladium on carbon (20 mg) and subjected to a hydrogen atmosphere. The mixture was stirred for a further 18 h and then filtered through a pad of Celite®. The pad was washed with methanol (50 mL) and the combined filtrates evaporatedin vacuoto give the crude residue which was purified by flash chromatography on silica eluting withCH2Cl2-methanol-aqueous ammonia (95:4.5:0.5) to give amine53(0.15 g, 87percent) as a brown solid; mp 89–92 °C (lit mp 94–95 °C); νmax/cm-13333, 3210, 1606, 1586, 1519, 1294, 1181;δH(500 MHz, CDCl3) 8.62 (1 H, dt,J1.0, 5.0 Hz), 7.83 (2 H, d,J8.5 Hz), 7.68–7.61 (2 H, m), 7.11 (1 H, m) 6.75 (2 H, d,J8.5 Hz), 3.83 (2 H, br s);δC(125 MHz, CDCl3) 157.6, 149.5, 147.5, 136.6, 129.8, 128.1, 121.0, 119.4, 115.2;m/z(ESI) 171 ([M + H]+, 100).
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 277 - 301
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988, vol. 24, # 11, p. 1221 - 1225[3] Khimiya Geterotsiklicheskikh Soedinenii, 1988, vol. 24, # 11, p. 1476 - 1480
[4] Molecular crystals and liquid crystals, 1980, vol. 62, # 1-2, p. 103 - 114
[5] Chemische Berichte, 1896, vol. 29, p. 168
[6] Journal of the Chemical Society, 1926, p. 2920[7] Journal of the Chemical Society, 1930, p. 398
[8] Journal of the Chemical Society, 1940, p. 1279,1283
[9] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 7, p. 818 - 829
[10] Patent: US2006/94644, 2006, A1, . Location in patent: Page/Page column 22
[11] Patent: WO2007/130743, 2007, A2, . Location in patent: Page/Page column 63
  • 2
  • [ 109-04-6 ]
  • [ 214360-73-3 ]
  • [ 18471-73-3 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; Step 4 [Show Image] 2-bromopyridine 5 (14.53 g, 92.0 mmol) and 4-aminophenylboronic acid pinacol ester (30.20 g, 138.0 mmol) were dissolved in dimethylformamide (200 ml). To the solution were added tetrakis triphenyl phosphine palladium (7.44 g, 6.4 mmol) and 2 M potassium carbonate solution (230 ml, 460 mmol) and the mixture was stirred for 2 hours at 100°C. The reactant was poured into water and filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and then saturated saline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography. To the obtained solid were added ethyl acetate and hexane and the deposited solid was collected with filtration to give the desired substituted aniline 6 (12.35 g, yield 79 percent). 1H-NMR (DMSO-d6) δppm: 5.42 (s, 2H), 6.63 (m, 2H), 7.14 (m, 1H), 7,69-7.75 (m, 2H), 7.79 (m, 2H), 8.51 (m, 1H).
79% With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; 2-bromopyridine 5 (14.53 g, 92.0 mmol) and 4-aminophenylboronic acid pinacol ester (30.20 g, 138.0 mmol) were dissolved in dimethylformamide (200 ml). To the solution were added tetrakis triphenyl phosphine palladium (7.44 g, 6.4 mmol) and 2 M potassium carbonate solution (230 ml, 460 mmol) and the mixture was stirred for 2 hours at 100° C. The reactant was poured into water and filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and then saturated saline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography. To the obtained solid were added ethyl acetate and hexane and the deposited solid was collected with filtration to give the desired substituted aniline 6 (12.35 g, yield 79percent).1H-NMR (DMSO-d6) δ ppm: 5.42 (s, 2H), 6.63 (m, 2H), 7.14 (m, 1H), 7.69-7.75 (m, 2H), 7.79 (m, 2H), 8.51 (m, 1H).
Reference: [1] Patent: EP2280000, 2011, A1, . Location in patent: Page/Page column 32
[2] Patent: US2011/28468, 2011, A1, . Location in patent: Page/Page column 20
[3] MedChemComm, 2017, vol. 8, # 1, p. 176 - 183
[4] Patent: WO2006/55951, 2006, A2, . Location in patent: Page/Page column 33
  • 3
  • [ 540-37-4 ]
  • [ 18471-73-3 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6985 - 6988
[2] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
  • 4
  • [ 109-09-1 ]
  • [ 106-40-1 ]
  • [ 18471-73-3 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 31, p. 6141 - 6146
[2] Tetrahedron, 1998, vol. 54, # 7, p. 1289 - 1298
  • 5
  • [ 109-04-6 ]
  • [ 540-37-4 ]
  • [ 18471-73-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 2, p. 286 - 297
  • 6
  • [ 106-40-1 ]
  • [ 18471-73-3 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
[2] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6985 - 6988
  • 7
  • [ 540-37-4 ]
  • [ 882521-96-2 ]
  • [ 18471-73-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 4, p. 685 - 687
  • 8
  • [ 1008-89-5 ]
  • [ 18471-73-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 7, p. 818 - 829
  • 9
  • [ 110-86-1 ]
  • [ 18471-73-3 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988, vol. 24, # 11, p. 1221 - 1225[2] Khimiya Geterotsiklicheskikh Soedinenii, 1988, vol. 24, # 11, p. 1476 - 1480
[3] Journal of the Chemical Society, 1926, p. 2920[4] Journal of the Chemical Society, 1930, p. 398
[5] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 277 - 301
  • 10
  • [ 100-05-0 ]
  • [ 18471-73-3 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1988, vol. 24, # 11, p. 1221 - 1225[2] Khimiya Geterotsiklicheskikh Soedinenii, 1988, vol. 24, # 11, p. 1476 - 1480
  • 11
  • [ 24067-17-2 ]
  • [ 18471-73-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 277 - 301
  • 12
  • [ 18471-73-3 ]
  • [ 51035-40-6 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1921, vol. 53, p. 217,223[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1024
[3] Molecular crystals and liquid crystals, 1980, vol. 62, # 1-2, p. 103 - 114
  • 13
  • [ 18471-73-3 ]
  • [ 4385-62-0 ]
Reference: [1] Journal of the Chemical Society, 1940, p. 355,357
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