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[ CAS No. 69045-79-0 ]

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Chemical Structure| 69045-79-0
Chemical Structure| 69045-79-0
Structure of 69045-79-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 69045-79-0 ]

CAS No. :69045-79-0 MDL No. :MFCD01863635
Formula : C5H3ClIN Boiling Point : -
Linear Structure Formula :- InChI Key :QWLGCWXSNYKKDO-UHFFFAOYSA-N
M.W :239.44 Pubchem ID :4397176
Synonyms :

Calculated chemistry of [ 69045-79-0 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.96
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.34
Log Po/w (MLOGP) : 2.01
Log Po/w (SILICOS-IT) : 3.05
Consensus Log Po/w : 2.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.43
Solubility : 0.0891 mg/ml ; 0.000372 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 1.01 mg/ml ; 0.00422 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.6
Solubility : 0.0606 mg/ml ; 0.000253 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.19

Safety of [ 69045-79-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 69045-79-0 ]

* 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 [ 69045-79-0 ]
  • Downstream synthetic route of [ 69045-79-0 ]

[ 69045-79-0 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 20511-12-0 ]
  • [ 69045-79-0 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
[2] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7493 - 7496
[3] Tetrahedron, 2002, vol. 58, # 14, p. 2885 - 2890
[4] Journal of the American Chemical Society, 2009, vol. 131, p. 3621 - 3630
[5] Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5228 - 5236
[6] Organic Letters, 2009, vol. 11, # 21, p. 4786 - 4789
[7] European Journal of Organic Chemistry, 2009, # 23, p. 3885 - 3894
[8] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 693 - 700
[9] Chemische Berichte, 1925, vol. 58, p. 116[10] Chem. Zentralbl., 1928, vol. 99, # I, p. 64
  • 2
  • [ 5350-93-6 ]
  • [ 69045-79-0 ]
YieldReaction ConditionsOperation in experiment
20% With hydrogen iodide; sodium nitrite In dichloromethane; water (a)
2-Chloro-5-iodopyridine
To a suspension of 5-amino-2-chloropyridine (2.56 g, 20 mmol) and hydriodic acid (57percent solution in water, 6.8 mL) in dichloromethane (50 mL) at 0° C. was added NaNO2 portionwise over 2 min.
The reaction was then stirred at 0° C. for a further 30 min and then poured into a mixture of dichloromethane and saturated sodium thiosulphate solution and the organic layer separated.
The aqueous layer was extracted further with dichloromethane (2*50 mL) and the combined organic extracts were dried over MgSO4, filtered and the solvents removed under reduced pressure.
Column chromatography of the residue on silica gel (dichloromethane as eluent) gave 2-chloro-5-iodopyridine as a colourless solid (930 mg, 20percent).
δH (300 MHz, CDCl3) 7.10 (1H, d, J=8.3), 7.88 (1H, dd, J=2.4 and 8.2), 8.55 (1H, d, J=2.0), ESMS 239 (MH+)
Reference: [1] Patent: US5976497, 1999, A,
  • 3
  • [ 53939-30-3 ]
  • [ 69045-79-0 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12425 - 12433
[2] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10480 - 10483
  • 4
  • [ 58757-38-3 ]
  • [ 69045-79-0 ]
Reference: [1] Nature Chemistry, 2018, vol. 10, # 10, p. 1016 - 1022
  • 5
  • [ 13472-79-2 ]
  • [ 69045-79-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
  • 6
  • [ 504-29-0 ]
  • [ 69045-79-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 3, p. 279 - 282
[2] Chemische Berichte, 1925, vol. 58, p. 116[3] Chem. Zentralbl., 1928, vol. 99, # I, p. 64
[4] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 693 - 700
  • 7
  • [ 142-08-5 ]
  • [ 69045-79-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
  • 8
  • [ 75-44-5 ]
  • [ 60154-05-4 ]
  • [ 69045-79-0 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1931, vol. 486, p. 71,78
  • 9
  • [ 69045-79-0 ]
  • [ 5350-93-6 ]
Reference: [1] Chemical Communications, 2008, # 26, p. 3052 - 3054
  • 10
  • [ 69045-79-0 ]
  • [ 13472-61-2 ]
Reference: [1] Chemische Berichte, 1925, vol. 58, p. 116[2] Chem. Zentralbl., 1928, vol. 99, # I, p. 64
  • 11
  • [ 69045-79-0 ]
  • [ 68-12-2 ]
  • [ 23100-12-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3427 - 3430
[2] Patent: WO2005/9479, 2005, A1, . Location in patent: Page/Page column 41
  • 12
  • [ 69045-79-0 ]
  • [ 41288-96-4 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 22, p. 4093 - 4096
  • 13
  • [ 69045-79-0 ]
  • [ 31301-51-6 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 19, p. 5134 - 5137
  • 14
  • [ 69045-79-0 ]
  • [ 68-12-2 ]
  • [ 114077-82-6 ]
Reference: [1] Patent: WO2006/41797, 2006, A2, . Location in patent: Page/Page column 47
  • 15
  • [ 69045-79-0 ]
  • [ 162318-34-5 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 693 - 700
  • 16
  • [ 69045-79-0 ]
  • [ 171197-80-1 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 8, p. 1866 - 1869
[2] Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12137 - 12145
  • 17
  • [ 69045-79-0 ]
  • [ 263012-63-1 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4170 - 4179
[2] Journal of Organic Chemistry, 2000, vol. 65, # 5, p. 1257 - 1272
[3] Journal of the American Chemical Society, 2011, vol. 133, # 17, p. 6780 - 6790
[4] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 4, p. 1062 - 1074
  • 18
  • [ 69045-79-0 ]
  • [ 444120-91-6 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 14, p. 2885 - 2890
  • 19
  • [ 69045-79-0 ]
  • [ 76-09-5 ]
  • [ 444120-94-9 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 14, p. 2885 - 2890
  • 20
  • [ 69045-79-0 ]
  • [ 100-51-6 ]
  • [ 84611-43-8 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9326 - 9333
  • 21
  • [ 69045-79-0 ]
  • [ 64-17-5 ]
  • [ 902837-52-9 ]
YieldReaction ConditionsOperation in experiment
60% for 12 h; Reflux 2-Chloro-5-iodopyridine (800 mg, 3.34 mmol, 1.0 eq.) was added to a solution of sodium (530 mg, 24.1 mmol, 7.2 eq.) in EtOH (15 ml) and the mixture was refluxed for 12 h. Ethanol was evaporated under reduced pressure and the residue was quenched with water. The reaction mixture was extracted with EtOAc (50 ml X 2). The combined organic layer was washed with water (20 ml X 3) and brine and dried over sodium sulfate. After removal of solvent, the residue was purified by column chromatography (silica gel 100-200 mesh, eluted with 2percent EtOAc-hexane) to afford 2-ethoxy-5- iodopyridine in 60percent yield.
Reference: [1] Patent: WO2010/127208, 2010, A1, . Location in patent: Page/Page column 58-59
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