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[ CAS No. 25700-12-3 ] {[proInfo.proName]}

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Chemical Structure| 25700-12-3
Chemical Structure| 25700-12-3
Structure of 25700-12-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 25700-12-3 ]

CAS No. :25700-12-3 MDL No. :MFCD18449274
Formula : C8H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :YJLYGWOUDNVDMM-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :11378567
Synonyms :

Calculated chemistry of [ 25700-12-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.36
TPSA : 30.71 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 0.82
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.53
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 1.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 1.7 mg/ml ; 0.0117 mol/l
Class : Very soluble
Log S (Ali) : -1.05
Solubility : 13.0 mg/ml ; 0.0897 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.53
Solubility : 0.427 mg/ml ; 0.00294 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.81

Safety of [ 25700-12-3 ]

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

Application In Synthesis of [ 25700-12-3 ]

* 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 [ 25700-12-3 ]
  • Downstream synthetic route of [ 25700-12-3 ]

[ 25700-12-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 288-13-1 ]
  • [ 626-55-1 ]
  • [ 25700-12-3 ]
YieldReaction ConditionsOperation in experiment
93% With copper(I) oxide; salicylaldehyde-oxime; caesium carbonate In acetonitrile for 24 h; Inert atmosphere; Reflux To a solution of copper(I) oxide (0.906 g, 6.33 mmol), salicylaldoximine (3.47 g, 25.3 mmol), 1H-pyrazole (12.93 g, 190 mmol), and cesium carbonate (66.0 g, 203 mmol) in acetonitrile (50.6 ml) under a nitrogen stream was added 3-bromopyridine (20 g, 127 mmol).
The reaction mixture was heated at reflux for 24H.
The reaction mixture was allowed to cool to ambient temperature, and then diluted with EtOAc, filtered through celite, and washed with H2O and saturated brine solution.
The organics were separated, dried with MgSO4, filtered and concentrated in vacuo.
The residue was purified by column chromatography eluting with 0-50percent acetone in hexanes to afford 3-(1H-pyrazol-1-yl)pyridine as a yellow oil (17 g, 93percent): 1H NMR (400 MHz, acetone-d6) δ 9.14 (d, J=2.2 Hz, 1H), 8.54 (d, J=3.8 Hz, 1H), 8.45 (dd, J=2.5, 0.5 Hz, 1H), 8.24 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.79 (d, J=1.5 Hz, 1H), 7.53 (ddd, J=8.3, 4.7, 0.7 Hz, 1H), 6.59 (dd, J=2.5, 1.8 Hz, 1H); EIMS m/z 145.
43% With caesium carbonate In acetonitrile at 80℃; for 24 h; Inert atmosphere Step 1:
Preparation of 3-pyrazol-1-yl-pyridine
To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere.
The reaction mass was refluxed for 24 hrs at 80° C.
The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43percent): 1H NMR (400 MHz, CDCl3) δ 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].
43% With copper(I) oxide; salicylaldehyde-oxime; caesium carbonate In acetonitrile at 80℃; for 24 h; Inert atmosphere To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO(16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under Natmosphere. The reaction mass was refluxed for 24 hrs at 80° C. The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43percent): 1H NMR (400 MHz, CDCl3) δ 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].
43% With copper(I) oxide; salicylaldehyde-oxime; caesium carbonate In acetonitrile at 80℃; for 24 h; Inert atmosphere Step 1:
Preparation of 3-pyrazol-1-yl-pyridine
To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere.
The reaction mass was refluxed for 24 hrs at 80° C.
The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43percent): 1H NMR (400 MHz, CDCl3) δ 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].
43% With copper(I) oxide; caesium carbonate; hydroxybenzaldoxime In acetonitrile at 80℃; for 24 h; Inert atmosphere Step 1:
Preparation of 3-pyrazol-1-yl-pyridine
To a solution of 3-bromopyridine (5 g, 0.031 mol) in 50 ml of acetonitrile were added pyrazole (2.6 g, 0.038 mol), Cs2CO3 (16.5 g, 0.050 mol), Cu2O (0.226 g, 0.0016 mol), and salicylaldoxime (0.867 g, 0.006 mol) under N2 atmosphere.
The reaction mass was refluxed for 24 hrs at 80° C.
The reaction mass was concentrated and the crude was purified by column chromatography using ethyl acetate and hexane (1:1) to afford the pyrazolyl pyridine as a dark brown liquid (2 g, 43percent): 1H NMR (400 MHz, CDCl3) δ 8.99 (d, J=2.8 Hz, 1H), 8.48 (dd, J=4.8, 1.2 Hz, 1H), 8.11-8.08 (m, 1H), 7.99 (d, J=1.2 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.38-7.35 (m, 1H), 6.53 (t, J=1.2 Hz, 1H); MS (m/z) 146 [M+1].

Reference: [1] European Journal of Organic Chemistry, 2004, # 4, p. 695 - 709
[2] Patent: US2012/220453, 2012, A1, . Location in patent: Paragraph 0164; 0165
[3] Synthesis (Germany), 2012, vol. 44, # 13, p. 2041 - 2048
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 13, p. 4101 - 4114
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 12, p. 4671 - 4684
[6] Green Chemistry, 2011, vol. 13, # 1, p. 42 - 45
[7] Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3158 - 3162
[8] Patent: US2012/110702, 2012, A1, . Location in patent: Page/Page column 15
[9] Patent: US2013/109566, 2013, A1, . Location in patent: Paragraph 0163; 0164
[10] Patent: US2013/288893, 2013, A1, . Location in patent: Paragraph 0191-0192
[11] Patent: US2016/60245, 2016, A1, . Location in patent: Paragraph 0191; 0192
  • 2
  • [ 288-13-1 ]
  • [ 1120-90-7 ]
  • [ 25700-12-3 ]
YieldReaction ConditionsOperation in experiment
83% With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 100℃; for 24 h; Inert atmosphere General procedure: The N-nucleophile (0.735mmol), Cu2O (0.0735mmol), Cs2CO3 (1.47mmol), DMSO (0.3mL) and heteroaryl halide (1.103mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100°C for 24h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of the products was confirmed by 1H, 13C NMR spectroscopic analysis and elemental analysis or mass spectroscopy.
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 42, p. 5868 - 5871
[2] Green Chemistry, 2011, vol. 13, # 1, p. 42 - 45
[3] Tetrahedron, 2013, vol. 69, # 35, p. 7279 - 7284
  • 3
  • [ 288-13-1 ]
  • [ 1120-90-7 ]
  • [ 25700-12-3 ]
  • [ 25700-13-4 ]
Reference: [1] Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 654 - 660
  • 4
  • [ 288-13-1 ]
  • [ 372-47-4 ]
  • [ 25700-12-3 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 1, p. 42 - 45
  • 5
  • [ 288-13-1 ]
  • [ 626-60-8 ]
  • [ 25700-12-3 ]
Reference: [1] Green Chemistry, 2011, vol. 13, # 1, p. 42 - 45
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