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[ CAS No. 142-08-5 ] {[proInfo.proName]}

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Chemical Structure| 142-08-5
Chemical Structure| 142-08-5
Structure of 142-08-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 142-08-5 ]

CAS No. :142-08-5 MDL No. :MFCD00462283
Formula : C5H5NO Boiling Point : -
Linear Structure Formula :- InChI Key :UBQKCCHYAOITMY-UHFFFAOYSA-N
M.W :95.10 Pubchem ID :8871
Synonyms :
α-Pyridone

Calculated chemistry of [ 142-08-5 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.06
TPSA : 32.86 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) : -7.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.06
Log Po/w (XLOGP3) : -0.58
Log Po/w (WLOGP) : 0.37
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.7
Solubility : 19.0 mg/ml ; 0.2 mol/l
Class : Very soluble
Log S (Ali) : 0.36
Solubility : 218.0 mg/ml ; 2.29 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -1.84
Solubility : 1.36 mg/ml ; 0.0143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 142-08-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P310+P330-P405 UN#:2811
Hazard Statements:H301-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 142-08-5 ]

* 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 [ 142-08-5 ]
  • Downstream synthetic route of [ 142-08-5 ]

[ 142-08-5 ] Synthesis Path-Upstream   1~59

  • 1
  • [ 142-08-5 ]
  • [ 4214-79-3 ]
Reference: [1] Synthesis, 2012, vol. 44, # 7, p. 1074 - 1078
  • 2
  • [ 110-86-1 ]
  • [ 109-00-2 ]
  • [ 142-08-5 ]
  • [ 626-64-2 ]
Reference: [1] Journal of Physical Chemistry, 1980, vol. 84, # 20, p. 2548 - 2551
  • 3
  • [ 142-08-5 ]
  • [ 13466-38-1 ]
Reference: [1] Patent: US5939439, 1999, A,
[2] Patent: WO2018/193387, 2018, A1, . Location in patent: Page/Page column 107
  • 4
  • [ 142-08-5 ]
  • [ 13466-38-1 ]
  • [ 13466-43-8 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
  • 5
  • [ 142-08-5 ]
  • [ 13472-79-2 ]
Reference: [1] Asian Journal of Chemistry, 2011, vol. 23, # 1, p. 41 - 43
[2] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
[3] Journal of Organic Chemistry, 1990, vol. 55, # 18, p. 5287 - 5291
  • 6
  • [ 142-08-5 ]
  • [ 13472-79-2 ]
Reference: [1] Chemische Berichte, 1925, vol. 58, p. 116[2] Chem. Zentralbl., 1928, vol. 99, # I, p. 64
  • 7
  • [ 142-08-5 ]
  • [ 5154-01-8 ]
Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3717
  • 8
  • [ 142-08-5 ]
  • [ 19365-07-2 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1984, vol. 317, # 4, p. 304 - 306
  • 9
  • [ 142-08-5 ]
  • [ 69045-79-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
  • 10
  • [ 142-08-5 ]
  • [ 13466-43-8 ]
YieldReaction ConditionsOperation in experiment
78% With bromine; potassium bromide In water at 20℃; for 24.25 h; 3-l3romo-pyridin-2-ol. A stirred suspension of 2-pyridone (77-0, 19 g, 200 mmol) in 200 mE of 1 M aqueous K13r at room temperature was treated over 15 mm with bromine (32 g, 200 mmol; CAUTION: Large quantities of 13r2 should be handled careffilly) in 200 mE of 1 M aqueous K13r, then stirred vigorously at room temperature 0/N. After 24 h, this solution deposited crystals which were filtered off and then recrystallized from acetonitrile to give 27.2 g (78percent) of 3-bromo- pyridin-2-ol. (77-1) [J. Am. Chem. Soc. 1982, 104, 4142- 4146; Bioorg. Med. Chem. Lett. 2002, 12, 197-200; JMed Chem. 1979, 22, 1284-1290.] Molecular weight calcd. for C5H4I3rNO: 173; (M+H) found: 174
Reference: [1] Patent: US2018/110824, 2018, A1, . Location in patent: Paragraph 0497; 0498; 0499
[2] Patent: US6110914, 2000, A,
  • 11
  • [ 142-08-5 ]
  • [ 13466-38-1 ]
  • [ 13466-43-8 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
  • 12
  • [ 142-08-5 ]
  • [ 16867-04-2 ]
Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985, vol. 24, p. 972 - 973
  • 13
  • [ 142-08-5 ]
  • [ 33630-99-8 ]
Reference: [1] Angewandte Chemie, 1936, vol. 49, p. 486,488
  • 14
  • [ 694-59-7 ]
  • [ 110-86-1 ]
  • [ 142-08-5 ]
  • [ 2739-97-1 ]
  • [ 366-18-7 ]
  • [ 109-97-7 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 5, p. 783 - 786
  • 15
  • [ 142-08-5 ]
  • [ 81971-38-2 ]
Reference: [1] Patent: US6465513, 2002, B1,
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 12, p. 4840 - 4860
  • 16
  • [ 142-08-5 ]
  • [ 13472-81-6 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
[2] Tetrahedron Letters, 1997, vol. 38, # 14, p. 2467 - 2470
[3] Patent: US5939439, 1999, A,
  • 17
  • [ 142-08-5 ]
  • [ 13472-81-6 ]
Reference: [1] Chemische Berichte, 1886, vol. 19, p. 2433
[2] Chemische Berichte, 1884, vol. 17, p. 590
  • 18
  • [ 7647-01-0 ]
  • [ 39856-50-3 ]
  • [ 142-08-5 ]
  • [ 13472-81-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 182,190
  • 19
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  • [ 13472-80-5 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 18, p. 4024 - 4032
[2] Tetrahedron Letters, 1997, vol. 38, # 14, p. 2467 - 2470
[3] Patent: US1753170, 1926, ,
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 2439
  • 20
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  • [ 13472-80-5 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2646
  • 21
  • [ 142-08-5 ]
  • [ 71597-85-8 ]
  • [ 51035-40-6 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 48, p. 12840 - 12842
  • 22
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  • [ 127406-56-8 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 16, p. 5692 - 5697
  • 23
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  • [ 30418-59-8 ]
  • [ 15889-32-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 48, p. 12840 - 12842
  • 24
  • [ 26482-54-2 ]
  • [ 7664-93-9 ]
  • [ 142-08-5 ]
  • [ 4214-76-0 ]
  • [ 4214-75-9 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 476[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1020
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1915, vol. 47, p. 1290[4] Chem. Zentralbl., 1916, vol. 87, # II, p. 15
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 345[6] Chemische Berichte, 1927, vol. 60, p. 2437
  • 25
  • [ 142-08-5 ]
  • [ 6332-56-5 ]
Reference: [1] Angewandte Chemie, 1936, vol. 49, p. 486,488
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987
  • 26
  • [ 142-08-5 ]
  • [ 5470-18-8 ]
Reference: [1] Russian Journal of General Chemistry, 2001, vol. 71, # 7, p. 1076 - 1087
  • 27
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  • [ 5470-18-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3983 - 3987
  • 28
  • [ 142-08-5 ]
  • [ 14529-54-5 ]
Reference: [1] Patent: WO2018/109050, 2018, A1,
[2] Organic Process Research and Development, 2018, vol. 22, # 8, p. 978 - 990
  • 29
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  • [ 58530-50-0 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 1, p. 2 - 3
  • 30
  • [ 142-08-5 ]
  • [ 58530-50-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 175,177
[2] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 175,177
[3] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 175,177
  • 31
  • [ 142-08-5 ]
  • [ 2980-33-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1921, vol. 53, p. 235,237[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1025
  • 32
  • [ 142-08-5 ]
  • [ 2980-33-8 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2013, vol. 49, # 7, p. 1000 - 1008[2] Khim. Geterotsikl. Soedin., 2013, vol. 49, # 7, p. 1073 - 1081,9
  • 33
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  • [ 142-08-5 ]
  • [ 25700-11-2 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 20, p. 8262 - 8269
[2] Chemistry of Materials, 2013, vol. 25, # 19, p. 3910 - 3920
  • 34
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  • [ 616-45-5 ]
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  • [ 541-59-3 ]
  • [ 123-56-8 ]
  • [ 109-97-7 ]
  • [ 3680-71-5 ]
  • [ 75-05-8 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2013, vol. 61, # 32, p. 7696 - 7704
  • 35
  • [ 1212-29-9 ]
  • [ 142-08-5 ]
  • [ 538-75-0 ]
Reference: [1] Tetrahedron Letters, 1985, vol. 26, # 13, p. 1661 - 1664
  • 36
  • [ 142-08-5 ]
  • [ 80-43-3 ]
  • [ 1003-56-1 ]
YieldReaction ConditionsOperation in experiment
85% at 120℃; Was added to the reactorPyridine-2-one 19-1 (0.095 g, 1 mmol)Dicumyl peroxide (0.81 g, 3 mmol) and 2 ml of acetic acid,120 ° C reaction, TLC followed the reaction until complete.The crude product obtained after the completion of the reaction was purified by column chromatography (petroleum ether: ethyl acetate = 1: 1)Separation and purification to give the target product 19-2 (yield 85percent).
Reference: [1] Patent: CN106496130, 2017, A, . Location in patent: Paragraph 0036; 0037
  • 37
  • [ 142-08-5 ]
  • [ 32315-10-9 ]
  • [ 1659-31-0 ]
YieldReaction ConditionsOperation in experiment
57% With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; ethyl acetate (b)
Dipyrid-2-ylcarbonate
Triethylamine (10.5 ml, 75 mmol) was added slowly to a solution of triphosgene (3.0 g, 10 mmol) and 2-hydroxypyridine (5.7 g, 60 mmol) in dry DCM (500 ml) at 0° C. under argon.
The mixture was allowed to warm to room temperature and was stirred overnight.
The solvent was removed under reduced pressure and the residue taken up in ethyl acetate (500 ml), washed with saturated aqueous sodium hydrogen carbonate (2*150 ml) and brine (200 ml), dried over anhydrous sodium sulphate filtered and concentrated to give an orange oil.
Crystallisation from ethyl acetate/hexane gave dipyrid-2-ylcarbonate as an off-white crystalline solid (3.70 g, 57percent).
deltaH 8.42 (2H, dd, J 4.8, 1.1 Hz), 7.83 (2H, ddd, J 7.8, 7.7, 1.8 Hz), 7.30-7.23 (4H, m).
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 24, p. 7452 - 7453
[2] Patent: US5563151, 1996, A,
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  • [ 75-44-5 ]
  • [ 1659-31-0 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 43, p. 4943 - 4946
[2] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575
  • 39
  • [ 142-08-5 ]
  • [ 52065-78-8 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1984, vol. 317, # 4, p. 304 - 306
[2] Archiv der Pharmazie (Weinheim, Germany), 1984, vol. 317, # 4, p. 304 - 306
  • 40
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  • [ 75-30-9 ]
  • [ 16096-13-2 ]
Reference: [1] Synthesis, 2009, # 16, p. 2725 - 2728
  • 41
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  • [ 24228-13-5 ]
YieldReaction ConditionsOperation in experiment
20% With tris[2-phenylpyridinato-C2,N]iridium(III); potassium acetate In acetonitrile at 20℃; for 6 h; Irradiation; Inert atmosphere; Glovebox; Schlenk technique General procedure: The reaction of 1a with 6ais representative (Table 2, entry 9). In a glovebox filled with nitrogen, Ir(ppy)3 (3.3 mg, 0.0050 mmol),Ph2IOTf (6a, 136.4 mg, 0.25 mmol), and potassium acetate (49.1 mg, 0.50 mmol) were placed in aSchlenk tube. The tube was sealed with a septum and then taken out of the glovebox. A solution ofN-methyl-2-pyridone (1a, 136.4 mg, 1.25 mmol) in MeCN (1 mL) was added using a syringe. Themixture was stirred for 6 h under blue light LED irradiation (12 DC/3 W). Water (20 mL) was added,and extraction was done with EtOAc (15 mL x 3). The combined organic phase was dried over sodium sulfate and then concentrated in vacuo. Purification via column chromatography (Wakosil C-200,hexane/EtOAc = 20/1 to EtOAc/CH2Cl2/Et3N = 1/1/0.05) followed by GPC provided pure1-methyl-3-phenylpyridin-2(1H)-one (7aa, 25.4 mg, 0.14 mmol, 55percent yield).
Reference: [1] Heterocycles, 2016, vol. 92, # 7, p. 1187 - 1203
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  • [ 59-88-1 ]
  • [ 24228-13-5 ]
Reference: [1] RSC Advances, 2015, vol. 6, # 1, p. 109 - 118
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  • [ 2488-15-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575
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  • [ 142-08-5 ]
  • [ 822-89-9 ]
  • [ 3029-19-4 ]
  • [ 91385-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
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  • [ 822-89-9 ]
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
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  • [ 822-89-9 ]
  • [ 3029-19-4 ]
  • [ 91385-15-8 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 10, p. 1927 - 1932
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  • [ 822-89-9 ]
  • [ 24463-15-8 ]
  • [ 91385-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
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  • [ 822-89-9 ]
  • [ 3029-19-4 ]
  • [ 24463-15-8 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 52, p. 9747 - 9750
  • 49
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  • [ 2592-18-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575
  • 50
  • [ 142-08-5 ]
  • [ 108-77-0 ]
  • [ 137-51-9 ]
Reference: [1] Patent: US4039523, 1977, A,
  • 51
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  • [ 142-08-5 ]
  • [ 20887-95-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 12, p. 3570 - 3575
  • 52
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  • [ 105125-43-7 ]
YieldReaction ConditionsOperation in experiment
91% With thionyl chloride; triethylamine In tetrahydrofuran (128-2)
Under nitrogen atmosphere, to a solution of 2-hydroxypyridine (2.66 g) and NEt3 (4.05 mL) in THF (80 mL) was added dropwise SOCl2 (1.05 mL) under ice-cooling, and the mixture was stirred for one hour.
The mixture was filtered, and the solvent was evaporated under reduced pressure to give di-2-pyridyl sulfite (3.02 g, 91percent).
91% With thionyl chloride; triethylamine In tetrahydrofuran (128-2)
Under nitrogen atmosphere, to a solution of 2-hydroxypyridine (2.66 g) and NEt3 (4.05 mL) in THF (80 mL) was added dropwise SOCl2 (1.05 mL) under ice-cooling, and the mixture was stirred for one hour.
The mixture was filtered, and the solvent was evaporated under reduced pressure to give di-2-pyridyl sulfite (3.02 g, 91 percent).
Reference: [1] Patent: US2003/181496, 2003, A1,
[2] Patent: EP1479384, 2004, A1,
[3] Tetrahedron Letters, 1986, vol. 27, # 17, p. 1925 - 1928
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  • [ 137628-17-2 ]
YieldReaction ConditionsOperation in experiment
45% With magnesium sulfate In <i>N</i>-methyl-acetamide; hexane EXAMPLE 1
2,3-Dibromo-5-chloropyridine (2)
3-bromo-5-chloropyridone (33.51 g, 161 mmol) was dissolved in dimethylformamide (251 ml) at ambient temperature.
Phosphorus (V) tribromide oxide (52.12 g, 182 mmol) was added and the reaction heated to 80° C. for 72 hours.
After cooling, the reaction was poured onto ice.
Vacuum filtration provided the product as a tan solid.
The crude product was taken up in ether and the pH of the water layer was adjusted to 13 with aqueous sodium hydroxide.
The aqueous layer was extracted three times with ether, the combined organic extracts treated with magnesium sulfate, and the solvent removed under vacuum.
The product was dissolved in boiling hexane and decolorizing carbon was added to the crude product, the contents heated to reflux and then filtered through celite.
The clear colorless filtrate was tripped under vacuum to yield the title compound as a white solid (18.1 g, 45percent), mp=39.5°-43° C.
The starting pyridone was recovered from the aqueous layer of the ether extraction by adjusting the pH to 1 with concentrated hydrochloric acid.
Filtration of the precipate and drying in a vacuum provided 13.8 g (40percent) of the starting pyridone. IR(neat): 3060, 1538, 1405, 1370, 1135, 1030, 905 cm-1. 1 H NMR Bruker 250 MHZ (CDCl3) δ: 8.28 (d, J=2 Hz); 7.89 (d, J=2 Hz).
13 C NMR (CDCl3) δ: 146.93, 141.45, 141.02, 131.34, 124.01.
Combustion analysis calculated for C5 H2 Br2 ClN: C, 22.13; H, 0.74; N, 5.16. Found: C, 21.93; H, 0.53; N, 4.90.
Reference: [1] Patent: US5436344, 1995, A,
  • 54
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  • [ 263012-63-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
  • 55
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  • [ 142-08-5 ]
  • [ 211555-30-5 ]
Reference: [1] Patent: US8053212, 2011, B1,
  • 56
  • [ 142-08-5 ]
  • [ 540-37-4 ]
  • [ 13143-47-0 ]
YieldReaction ConditionsOperation in experiment
95% With 8-quinolinol; potassium carbonate In N,N-dimethyl-formamideInert atmosphere; Reflux; Large scale In a 3000L reactor, iodoaniline 438kg, 2-hydroxypyridine 190kg, 8-hydroxyquinoline 58kg, potassium carbonate 207kg, N,N-dimethylformamide (DMF) 1500kg, nitrogen protection, stirring is turned on. The mixture was warmed to reflux and reacted overnight. Chromatography was followed up to the end of the reaction. The potassium iodide was removed by filtration. Part of the DMF was recovered under reduced pressure, cooled to 50° C., and filtered to give crude 1-(4-aminophenyl)-1H-pyridin-2-one. The crude product was added with 740 kg of ethanol, heated and dissolved, and 55 kg of activated carbon was added for decoloration. The solution was filtered while hot, and the filtrate was cooled and crystallized. The product was filtered, dried and packaged to give 1-(4-aminophenyl)-1H-pyridin-2-one with a yield of 95. percent,The purity is 99percent.
70% With copper(l) iodide; 8-quinolinol; caesium carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 15 h; Sealed tube 11128] In a similar manner as described in Example 114,(R)-5-(3-(4-methoxybenzamido)piperidin- 1 -yl)-3-(4-(2-ox-opyridin- 1 (2H)-yl)phenylamino)pyrazine-2-carboxamide(154) was prepared using 1 -(4-aminophenyl)pyridin-2(1H)-one. MS found for C29H29N704 as (M+H) 540.1, (M—H)538.3. UV: X=260, 285, 308, 346, 369 nm Synthesis of i-(4-aminophenyl)pyridin-2(1H)-one: The mixture of 4-iodoa-niline (1.00 g, 4.56 mmol), 2-hydroxypyridine (650 mg, 6.84mmol), fine powder Cs2CO3 (2.97 g, 9.12 mmol), fine powderCul (180mg, 0.92 mmol), 8-hydroxyquinoline (140mg, 0.92mmol) in 6 mE DMSO and 10 mE dioxane was stirred in asealed tube at 120° C. for 15 h. The mixture was diluted with300 mE EtOAc, filtered through celite, washed with brine,dried, concentrated and subjected to flash column with 0 to7percent MeOR in dichioromethane to isolate this compound (590mg, yield 70percent).
53.45% With copper(l) iodide; 8-quinolinol; potassium carbonate In dimethyl sulfoxide at 130℃; for 12 h; Inert atmosphere General procedure: Compound 1 (5g, 22.83mmol) was dissolved in DMSO (120mL), followed by the addition of 2-Piperidinone (4.53g, 45.66mmol), CuI (0.43g, 2.28mmol), 8-hydroxy-quinoline (0.66g, 4.57mmol) and K2CO3 (9.46g, 68.49mmol). The mixture was heated to 130°C under N2 for 12h, cooled, and quenched with water (120mL). The organics were extracted with ethyl acetate (2×150mL) and dried (Na2SO4). Purification by silica gel column chromatography (n-hexane/ethyl acetate, 5/1 to 3/1, as eluent) afforded compound 2 as faint yellow (2.80g, 64.47percent).
39.8% With copper(l) iodide; 8-quinolinol; caesium carbonate In dimethyl sulfoxide at 120℃; A mixture of pyridin-2-ol (2.00 g, 21.0 mmol), 4-iodoaniline (4.61 g, 21.0 mmol), 8-quinolinol (0.61 g, 4.2 mmol), Cul (0.80 g, 4.2 mmol) and Cs2C03 (10.26 g, 31.5 mmol) in DMSO (50 mL) was stirred at 120°C for overnight. After filtration, the filtrate was partitioned between EA and water and the aqueous layer was further extracted with EA. The combined organic layers was washed with water and brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound as a green solid (1.56 g, 39.8 percent yield). MS (m/z): 186.9 (M+H)+.
39.8% With copper(l) iodide; 8-quinolinol; caesium carbonate In dimethyl sulfoxide at 120℃; A mixture of pyridin-2-ol (2.00 g, 21.0 mmol), 4-iodoaniline (4.61 g, 21.0 mmol), 8-quinolinol (0.61 g, 4.2 mmol), Cul (0.80 g, 4.2 mmol) and Cs2C03 (10.26 g, 31.5 mmol) in DMSO (50 mL) was stirred at 120°C for overnight. After filtration, the filtrate was partitioned between EA and water and the aqueous layer was further extracted with EA. The combined organic layers was washed with water and brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound as a green solid (1.56 g, 39.8 percent yield). MS (m/z): 186.9 (M+H)+.

Reference: [1] Patent: CN107382836, 2017, A, . Location in patent: Paragraph 0021; 0022
[2] Patent: US2015/158865, 2015, A1, . Location in patent: Paragraph 1127; 1128
[3] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 411 - 422
[4] Patent: WO2014/139145, 2014, A1, . Location in patent: Page/Page column 37
[5] Patent: WO2014/139465, 2014, A1, . Location in patent: Page/Page column 38
[6] Patent: WO2006/55951, 2006, A2, . Location in patent: Page/Page column 59
[7] Patent: WO2008/86226, 2008, A2, . Location in patent: Page/Page column 123-124
[8] Patent: WO2005/32468, 2005, A2, . Location in patent: Page/Page column 158
[9] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 118
[10] Patent: WO2006/63293, 2006, A2, . Location in patent: Page/Page column 48-49
[11] Patent: WO2005/32468, 2005, A2, . Location in patent: Page/Page column 158
  • 57
  • [ 142-08-5 ]
  • [ 13143-47-0 ]
Reference: [1] Patent: WO2014/135471, 2014, A1,
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  • [ 2314-97-8 ]
  • [ 22245-83-6 ]
YieldReaction ConditionsOperation in experiment
50% With ferrocene; dihydrogen peroxide; dimethyl sulfoxide In water at 40 - 50℃; for 0.333333 h; 0.19 g (2.0 mmol) of 2-hydroxypyridine and 0.11 g (0.6 mmol) of ferrocene were weighed and placed in a two-neck flask and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 8.0 ml of dimethyl sulfoxide, 2.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide and 0.4 ml of a 30percent hydrogen peroxide aqueous solution, and the mixture was stirred for 20 minutes. During the stirring, the temperature of the reaction system rose up in the range of from 40°C to 50°C. Thereafter, the resulting solution was cooled to room temperature. Formation of 2-hydroxy-3-trifluoromethylpyridine (19F-NMR yield: 64percent) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. The subsequent procedure was conducted in the same manner as in Example 1 and 2-hydroxy-3-trifluoromethylpyridine was obtained as a white solid (0.081 g, yield: 50percent). 1H-NMR(deuterated chloroform):δ6. 34(dd, J=6. 9, 5. 6Hz, 1H), 7. 65 (d, J=5. 6Hz, 1H), 7. 88 (d, J=6. 9Hz, 1H), 13. 25 (brs, 1H). 13C-NMR(deuterated chloroform):δ105. 6, 120. 4(q, JCF=31. 4H z), 122. 7(q, JCF=271. 3Hz), 139. 2, 140. 7(q, JCF=4. 9Hz), 161. 4. 19F-NMR(deuterated chloroform):δ-66. 0. MS(m/z):163[M]+.
Reference: [1] Patent: EP2080744, 2009, A1, . Location in patent: Page/Page column 7-8
[2] Journal of Fluorine Chemistry, 2010, vol. 131, # 1, p. 98 - 105
  • 59
  • [ 142-08-5 ]
  • [ 141699-59-4 ]
  • [ 887928-35-0 ]
Reference: [1] Patent: WO2006/55951, 2006, A2, . Location in patent: Page/Page column 64
[2] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 123
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