Home Cart 0 Sign in  
X

[ CAS No. 25797-03-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 25797-03-9
Chemical Structure| 25797-03-9
Chemical Structure| 25797-03-9
Structure of 25797-03-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 25797-03-9 ]

Related Doc. of [ 25797-03-9 ]

Alternatived Products of [ 25797-03-9 ]

Product Details of [ 25797-03-9 ]

CAS No. :25797-03-9 MDL No. :MFCD09908215
Formula : C13H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :MHTVGGZESFVQIQ-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :11310078
Synonyms :

Calculated chemistry of [ 25797-03-9 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.53
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.88
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 3.23
Log Po/w (MLOGP) : 2.14
Log Po/w (SILICOS-IT) : 3.6
Consensus Log Po/w : 2.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.44
Solubility : 0.0708 mg/ml ; 0.000365 mol/l
Class : Soluble
Log S (Ali) : -2.99
Solubility : 0.2 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.43
Solubility : 0.00072 mg/ml ; 0.00000371 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.91

Safety of [ 25797-03-9 ]

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 [ 25797-03-9 ]

* 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 [ 25797-03-9 ]
  • Downstream synthetic route of [ 25797-03-9 ]

[ 25797-03-9 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 945607-88-5 ]
  • [ 25797-03-9 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With pyridine N-oxide; phosphorus trichloride In chloroform at 80℃; for 7 h;
Stage #2: With sodium hydrogencarbonate In chloroform; water at 0℃; for 0.5 h;
Phosphorus trichloride (0.02 niL, d 1.57, 0.22 mmol) was added dropwise to a stirred solution of the pyridine N-oxide (12 mg, 0.038 mmol) in CHCl3 (1 mL). The reaction mixture was heated to 80 °C for 7 h. Ice was added to the reaction mixture and then15 neutralized to pH 10 using saturated aqueous NaHCO3 solution. After stirring for 30 min, the mixture was extracted using CHCl3 (3 x 15 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified using chromatography eluting with 100percent EtOAc to 10percent MeOH/EtOAc to give the product as a white solid (6 mg, 0.03 mmol, 80percent). mp: 250-252 °C. ER (neat, cm"1):20 3439, 1642. 1H NMR (400 MHz, MeOD) δ 7.23 (IH, s), 6.58 (IH, d, J - 5.7 Hz), 6.29 (2H, d, J = 7.7 Hz), 5.93 (2H, t, J= 7.5 Hz), 5.89 (IH, d, J= 5.9 Hz), 5.82 (IH, t, J= 7.3 Hz), 5.45 (IH, s). 13C NMR (100 MHz, MeOD) δ 143.5, 142.8, 141.9, 140.5, 133.2, 130.3, 129.5, 127.9, 126.8, 108.1, 99.1, 99.1. HRMS (ESI): calc'd for Ci3H10N2 ([M]+) 194.0844. Found: 194.0852
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5152 - 5160
[2] Patent: WO2008/22467, 2008, A1, . Location in patent: Page/Page column 138
  • 2
  • [ 288254-71-7 ]
  • [ 25797-03-9 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 13, p. 2187 - 2193
[2] Angewandte Chemie - International Edition, 2000, vol. 39, # 14, p. 2488 - 2490
[3] Tetrahedron, 2003, vol. 59, # 9, p. 1571 - 1587
[4] Patent: EP1452525, 2004, A1, . Location in patent: Page 22
  • 3
  • [ 38240-21-0 ]
  • [ 536-74-3 ]
  • [ 25797-03-9 ]
YieldReaction ConditionsOperation in experiment
68% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; copper(I) thiophene-2-carboxylate; 1,3-bis-(diphenylphosphino)propane; triethylamine In tetrahydrofuran at 100℃; for 15 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: Pyridine-2-thione (0.1 mmol), CuTC (0.1 mmol), CuI (0.05mol),Pd(PPh3)2Cl2 (0.005mol), dppp (0.02 mmol), phenyl-acetylene (0.3 mmol), Et3N (3 mL) and THF (3 mL) were added to a 35 mL sealed tube and stirred at 100 °C for 15 h under argon atmosphere. The reaction mixture was then cooled to room temperature and then diluted with EtOAc (25 mL) and filtered through celite with EtOAc (50 mL). The crude products were purified by flash column chromatography on a silica gel column with petroleum ether/ethylacetate as the eluent to afford the corresponding purified products.
Reference: [1] Tetrahedron, 2017, vol. 73, # 37, p. 5485 - 5492
  • 4
  • [ 39856-58-1 ]
  • [ 536-74-3 ]
  • [ 25797-03-9 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; di(1-adamantyl)benzylphosphonium hydrobromide In dimethyl sulfoxide at 100℃; for 1 h; Schlenk technique; Inert atmosphere
Stage #2: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 100℃; for 0.25 h; Schlenk technique; Inert atmosphere
General procedure: 3-Amino-2-bromopyridine (1a) (87 mg, 0.5 mmol) or2-bromoaniline (1b) (172 mg, 1.00 mmol), Pd(PPh3)2Cl2(9.0 mg, 13 mmol or 17.5 mg, 25.0 mmol), and(1-Ad)2PBn·HBr (12 mg, 25 mmol or 23.6 mg, 50.0 mmol)were placed into a dry screw-cap Schlenk tube with amagnetic stirring bar, and the vessel was evacuated. Afterflushing the vessel with nitrogen, dry DMSO (1.0 or 1.5 ml),the corresponding alkyne 2a–j (0.6 mmol or 1.2 mmol),and DBU (225 mg, 1.50 mmol or 457 mg, 3.00 mmol)were added. The reaction mixture was stirred at 100°Cunder nitrogen for 1 h until the bromide was completelyconsumed (monitored by TLC). After cooling to roomtemperature, KOt-Bu (253 mg, 2.25 mmol or 281 mg,2.50 mmol) and DMSO (0.50 or 1.00 ml) were added to thereaction mixture, and the mixture was stirred at 100°Cunder nitrogen for 0.25 h. After cooling to roomtemperature, deionized water or brine (20 ml) was added tothe mixture. The aqueous layer was extracted several timeswith EtOAc or CH2Cl2. The combined organic phases weredried over anhydrous Na2SO4 and after filtration, thesolvents were removed under reduced pressure. The residuewas purified by flash chromatography on silica gel to givethe analytically pure products 3a–j. 2-Phenyl-1H-pyrrolo[3,2-b]pyridine (3a) was synthesizedfrom 3-amino-2-bromopyridine (1a) (87 mg, 0.5 mmol)and phenylacetylene (2a) (61 mg, 0.6 mmol), eluent forflash chromatography EtOAc–n-hexane, 3:2. Yield 53 mg(55percent), beige solid, mp 249°C. IR spectrum, ν, cm–1: 3082(w), 3053 (w), 3011 (w), 2969 (w), 2932 (w), 1603 (w),1568 (w), 1537 (w), 1481 (w), 1456 (m), 1414 (m), 1362 (m),1343 (m), 1289 (w), 1275 (m), 1227 (w), 1200 (w), 1173 (w),1157 (w), 1119 (w), 1096 (w), 1074 (w), 1053 (w), 1030 (w),988 (w), 924 (m), 910 (w), 833 (w), 810 (w), 785 (m), 766 (s),735 (m), 687 (s). 1H NMR spectrum, δ, ppm (J, Hz): 7.06(1H, s, H-3); 7.10 (1H, dd, J = 8.0, J = 4.6, H-6); 7.37–7.38(1H, m, H Ph); 7.48–7.50 (2H, m, H Ph); 7.77 (1H, d, J = 8.0, H-7); 7.92–7.93 (2H, m, H Ph); 8.31–8.32 (1H, m,H-5); 11.82 (1H, br. s, NH). 13C NMR spectrum, δ, ppm:99.2 (CH); 116.8 (CH); 118.3 (CH); 125.5 (CH); 128.4(CH); 129.2 (CH); 130.1 (C); 131.7 (C); 141.1 (C); 142.9(CH); 146.9 (C). Mass spectrum, m/z (Irel, percent): 195 (14),194 [M]+ (100), 193 (25), 192 (7), 167 (6), 166 (8), 97 (11).Found, m/z: 195.0920 [M+H]+. C13H11N2. Calculated, m/z:195.0917.
Reference: [1] Chemistry of Heterocyclic Compounds, 2018, vol. 54, # 3, p. 334 - 338[2] Khim. Geterotsikl. Soedin., 2018, vol. 54, # 3, p. 334 - 338,5
  • 5
  • [ 39856-58-1 ]
  • [ 98-81-7 ]
  • [ 25797-03-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 13, p. 3250 - 3253
  • 6
  • [ 627510-86-5 ]
  • [ 25797-03-9 ]
Reference: [1] Synthesis, 2003, # 11, p. 1671 - 1678
  • 7
  • [ 945607-69-2 ]
  • [ 25797-03-9 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5152 - 5160
  • 8
  • [ 945607-84-1 ]
  • [ 25797-03-9 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5152 - 5160
  • 9
  • [ 945607-87-4 ]
  • [ 25797-03-9 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 14, p. 5152 - 5160
  • 10
  • [ 6298-19-7 ]
  • [ 25797-03-9 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 9, p. 1571 - 1587
  • 11
  • [ 39856-58-1 ]
  • [ 98-86-2 ]
  • [ 25797-03-9 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5316 - 5319
  • 12
  • [ 123846-65-1 ]
  • [ 98-80-6 ]
  • [ 25797-03-9 ]
Reference: [1] Synlett, 2012, vol. 23, # 17, p. 2511 - 2515,5
[2] Synlett, 2012, vol. 23, # 17, p. 2511 - 2515
  • 13
  • [ 5470-18-8 ]
  • [ 25797-03-9 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 13, p. 2187 - 2193
  • 14
  • [ 627510-84-3 ]
  • [ 25797-03-9 ]
Reference: [1] Synthesis, 2003, # 11, p. 1671 - 1678
  • 15
  • [ 627510-85-4 ]
  • [ 25797-03-9 ]
Reference: [1] Synthesis, 2003, # 11, p. 1671 - 1678
  • 16
  • [ 462-08-8 ]
  • [ 25797-03-9 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 1996, vol. 32, # 2, p. 202 - 205
  • 17
  • [ 947330-58-7 ]
  • [ 25797-03-9 ]
Reference: [1] Synthetic Communications, 2007, vol. 37, # 13, p. 2187 - 2193
  • 18
  • [ 36052-27-4 ]
  • [ 25797-03-9 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 59, p. 9283 - 9286
  • 19
  • [ 1462-86-8 ]
  • [ 25797-03-9 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 59, p. 9283 - 9286
  • 20
  • [ 824429-51-8 ]
  • [ 25797-03-9 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 59, p. 9283 - 9286
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 25797-03-9 ]

Aryls

Chemical Structure| 61327-59-1

[ 61327-59-1 ]

2-Phenyl-1,5-naphthyridine

Similarity: 0.93

Chemical Structure| 40068-81-3

[ 40068-81-3 ]

2-(Naphthalen-2-yl)-1H-pyrrolo[2,3-c]pyridine

Similarity: 0.91

Chemical Structure| 2922-07-8

[ 2922-07-8 ]

2-Phenyl-1H-pyrrolo[2,3-c]pyridine

Similarity: 0.91

Chemical Structure| 1173285-69-2

[ 1173285-69-2 ]

6-Phenyl-5H-pyrrolo[3,2-d]pyrimidine

Similarity: 0.89

Chemical Structure| 61327-60-4

[ 61327-60-4 ]

2-Phenyl-1,7-naphthyridine

Similarity: 0.89

Related Parent Nucleus of
[ 25797-03-9 ]

Other Aromatic Heterocycles

Chemical Structure| 40068-81-3

[ 40068-81-3 ]

2-(Naphthalen-2-yl)-1H-pyrrolo[2,3-c]pyridine

Similarity: 0.91

Chemical Structure| 2922-07-8

[ 2922-07-8 ]

2-Phenyl-1H-pyrrolo[2,3-c]pyridine

Similarity: 0.91

Chemical Structure| 1173285-69-2

[ 1173285-69-2 ]

6-Phenyl-5H-pyrrolo[3,2-d]pyrimidine

Similarity: 0.89

Chemical Structure| 37388-07-1

[ 37388-07-1 ]

2-Phenyl-1H-pyrrolo[3,2-c]pyridine

Similarity: 0.87

Chemical Structure| 3837-42-1

[ 3837-42-1 ]

1,3-Diphenylbenzo[f]quinoline

Similarity: 0.83