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[ CAS No. 39774-26-0 ] {[proInfo.proName]}

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Chemical Structure| 39774-26-0
Chemical Structure| 39774-26-0
Structure of 39774-26-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 39774-26-0 ]

CAS No. :39774-26-0 MDL No. :MFCD00234691
Formula : C11H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :XIYPPJVLAAXYAB-UHFFFAOYSA-N
M.W : 234.09 Pubchem ID :568679
Synonyms :

Calculated chemistry of [ 39774-26-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.37
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.43
Log Po/w (XLOGP3) : 3.54
Log Po/w (WLOGP) : 3.51
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.2

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.14
Solubility : 0.017 mg/ml ; 0.0000727 mol/l
Class : Moderately soluble
Log S (Ali) : -3.5
Solubility : 0.0748 mg/ml ; 0.00032 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.00093 mg/ml ; 0.00000397 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.06

Safety of [ 39774-26-0 ]

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 [ 39774-26-0 ]

* 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 [ 39774-26-0 ]
  • Downstream synthetic route of [ 39774-26-0 ]

[ 39774-26-0 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 626-05-1 ]
  • [ 98-80-6 ]
  • [ 39774-26-0 ]
YieldReaction ConditionsOperation in experiment
93% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane; water at 40℃; for 1 h; Inert atmosphere 2-Bromo-6-phenylpyridine 2,6-Dibromopyridine (2 g, 8.44 mmol), phenylboronic acid (1 .03 g, 8.44 mmol), potassium carbonate (4.67 g, 33.77 mmol) and TBAB (271 mg, 0.84 mmol) were combined in a mixture of 1 ,4-dioxane (16 ml) and water (4 ml). The reaction mixture was degassed by bubbling nitrogen through for 30 min prior to the addition of PdCI2(dppf) (62 mg, 0.084 mmol). The reaction mixture was stirred at 40 °C for 1 h before being filtered through celite. The filtrate was collected and the solvent removed. The crude material was then purified by column chromatography, eluting 100percent petroleum spirits to give the title compound as a colourless solid (1 .85 g, 93percent). 1H NMR (400 MHz, DMSO) δ 8.56 (dd, J= 6.3, 2.4 Hz, 1 H), 8.36 - 8.18 (m, 2H), 8.16 - 8.00 (m, 2H), 7.61 - 7.53 (m, 2H), 7.53 - 7.45 (m, 1 H).
74% With potassium carbonate In 1,2-dimethoxyethane; water for 24 h; Inert atmosphere; Reflux A mixture of 2,6-dibromopyridine (2.36 g, 10 mmol), phenylboronic acid (1.0 eq), Pd(OAc)2 (0.05 equiv), and PPh3 (0.2 equiv) were dissolved in dimethoxyethane/2M K2CO3 aqueous solution (80 rnL, 1 :1) under nitrogen atmosphere. The mixture was heated and refluxed for 24h. After being cooled to room temperature, the reaction mixture was diluted with EtOAc, and poured into a brine solution. The organic layer was separated, washed with the water, dried, and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to obtain the pure product Ph- Py-Br in 74percent yield. 1H NMR (CDCl3): .pound. 7.41-7.51 (m, 4H), 7.60 (dd, IH), 7.70 (dd, IH), 8.00 (dd, 2H).
34% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 3 h; Inert atmosphere; Reflux 1L round bottom flask equipped with in-flown plugging of the condensing tube, a nitrogen inlet port, one of the and 2, 6-dibromopyridine (15. 3 g, 64. 58 mmol), phenyl boronic acid (7. 87 g, 64. 58 mmol), and potassium carbonate (17. 58 g, 129. 16 mmol) a, 228 ml of water is added and 150 ml dimethoxyethane. The mixed nitrogen bubbling directly 15 minutes. Tetrakisphenol palladium (triphenylphosgene) (0) (1. 85 g, 1. 60 mmol) is added, the reaction mixture is heated to reflux. 3 after the completion of heating the reaction time. It is cooled to room temperature, water and diluted with ethyl acetate. Separating layer, a water layer is extracted with ethyl acetate. The organic layer is dried on magnesium sulfate, filtered, the solvent is evaporated. The substance is, 2percent ethyl acetate/hydroxyhexanamide column chromatography eluted and, subsequently, to collect the product 150 °C kouguell roll is used in a vacuum purified by distillation. 5. The obtained product of 2g (34percent).
15% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; tolueneInert atmosphere; Reflux Pitching 2 L flask, 2,6-dibromo-pyridine (2,6-dibromopyridine) 5g (0.0213mol), phenylboronic acid (phenylboronic acid) in1.3g (0.0106mol) and Pd (PPh3) 4 put 0.367g (0.32mmol) for the 36 mL Toluene 700 mL EtOH, and under a nitrogen atmosphereAfter the hash Keene, by the addition of 2M K2CO3 solution 10mL and stirred under reflux. After the reaction was terminated to cool to room temperature and 20mL H2OIt was added. Drying the mixture and then extracted twice with EtOAc 50 mL extract with Na2SO4, filtered and concentrated under a reduced pressure.Purification of the resulting compound by silica gel column chromatography to give 0.38 g compound (Intermediate 8) (yield: 15percent) of a white solid was obtained.
2.7 g With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In water; N,N-dimethyl-formamide at 80℃; Inert atmosphere To a mixture of 2,6-dibromopyridine (3.50 g, 14.8 mmol) and phenylboronic acid (1.80 g, 14.8 mmol) in N,N-dimethylformamide (20 mL) at room temperature under nitrogen, a solution of tribasic potassium phosphate (7.80 g, 36.7 mmol) in water (14 mL) and bis(triphenylphoshine)palladium(II) dichloride (518 mg, 0.74 mmol) were added.
The mixture was deoxygenated (toggle between vacuum and nitrogen gas 5 times) and heated to 80° C. overnight.
The mixture was cooled, diluted with ethyl acetate, and washed with water and brine.
The organic layer was dried, filtered and concentrated.
The residue was purified by column chromatography on silica gel, eluting with 5percent ethyl acetate in hexanes to give a mixture containing 2-bromo-6-phenylpyridine (21-1, 2.70 g) that was used without further purification.

Reference: [1] Patent: WO2015/172196, 2015, A1, . Location in patent: Paragraph 0033; 00179; 00200
[2] Patent: WO2009/111299, 2009, A2, . Location in patent: Page/Page column 23
[3] Patent: JP5832992, 2015, B2, . Location in patent: Paragraph 0139; 0140
[4] Patent: KR2015/137230, 2015, A, . Location in patent: Paragraph 0113; 0114; 0115
[5] Patent: US2004/171614, 2004, A1,
[6] Patent: US2005/85506, 2005, A1,
[7] Patent: US2011/82164, 2011, A1, . Location in patent: Page/Page column 32
[8] Dalton Transactions, 2017, vol. 46, # 10, p. 3160 - 3169
[9] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2018, vol. 73, # 11, p. 885 - 893
[10] Patent: US2018/312523, 2018, A1, . Location in patent: Paragraph 1828; 1829
  • 2
  • [ 1008-89-5 ]
  • [ 39774-26-0 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With n-butyllithium; 2-(N,N-dimethylamino)athanol In hexane at -10℃; for 1 h;
Stage #2: With ethylene dibromide In tetrahydrofuran; hexane at -40 - 20℃;
Butyllithium (50 mL, 118 mmol), hexanes (100 mL) and dimethylaminoethanol (5.91 mL, 59.0 mmol) were combined and cooled to -10°C, 2-Phenylpyridine (7.63 g, 49.2 mmol) was added dropwise over 5 minutes to form a clear orange solution. After 1 h, the solution had darkened to red-orange. The solution was then cooled to -40°C and THF (500 mL) that had been cooled to -35°C was added. Immediately 1,2-dibromoethane (25.4 mL, 295 mmol) was added in one portion, and the mixture was warmed to ambient temperature. The volatiles were removed by evaporation and the yellow oily paste was dissolved in Et^O (125 mL) and water (100 mL). The aqueous layer was removed and the organics were dried over brine, then sodium sulfate. Evaporation of the ether afforded crude product that was crystallized from hexanes as yellow crystals (8.0 g, 69percent).
48%
Stage #1: With n-butyllithium; 2-(N,N-dimethylamino)athanol In n-heptane at 0℃; for 1 h;
Stage #2: With carbon tetrabromide In n-heptane at -78 - 20℃;
To N,N-dimethylethanolamine (0.8 mL, 8.00 mmol) in heptane (10 mL) cooled externally to 0° C. was added dropwise a 2.5 M n-butyllithium solution (6.40 mL) and the reaction mixture stirred for 30 minutes. 2-Phenylpyridine (12) (412 mg, 2.66 mmol) in heptane (5 mL) was then added and the reaction mixture stirred for a further 1 hour. The reaction was then cooled and carbon tetrabromide (3.18 g, 9.60 mmol) was added whilst maintaining the temperature at -78° C. The reaction was kept at -78° C. for 1 hour and then allowed to warm to ambient temperature. Water was cautiously added and extracted with TBME (.x.2), dried (Na2SO4) and the solvent concentrated in vacuo. The crude product was purified by column chromatography eluting with 5percent EtOAc in heptane to give the title compound. Yield: 300 mg, 48percent; LC-MS 41.63 min; HPLC Purity: 97percent; MS (ES+) m/z 234, 236 (M+H)
Reference: [1] European Journal of Organic Chemistry, 2008, # 12, p. 2049 - 2055
[2] Journal of Organic Chemistry, 2003, vol. 68, # 5, p. 2028 - 2029
[3] Patent: WO2017/3565, 2017, A1, . Location in patent: Paragraph 0137
[4] Patent: US2010/130556, 2010, A1, . Location in patent: Page/Page column 21
[5] Journal of the American Chemical Society, 1956, vol. 78, p. 5842
[6] Patent: EP1683804, 2006, A2, . Location in patent: Page/Page column 19
  • 3
  • [ 626-05-1 ]
  • [ 98-80-6 ]
  • [ 39774-26-0 ]
  • [ 3558-69-8 ]
YieldReaction ConditionsOperation in experiment
80% With (+/-)-7-(2,3-diacetoxypropyl)theophylline; palladium diacetate; lithium carbonate In water at 120℃; for 0.166667 h; Microwave irradiation; Green chemistry General procedure: Suzuki–Miyaura couplings were performed in glass tubes suitable for microwave. Halopyridines (0.44 mmol), phenyl boronic acid (65.17 mg, 0.53 mmol), Li2CO3 (63.7 mg, 0.89 mmol), 1 mol percent of Pd(OAc)2 (1 mg, 4.45 ϰ 10-3 mol), and 2 mol percent of the corresponding ligand in 3 mL of distilled water. The mixtures were stirred and heated at 120 °C under microwave radiation during 10 min with a ramp of 1 min in a CEM Discover reactor coupled to a CEM Explorer robotic system. The resulting reaction mixture was cooled to room temperature and the mixture extracted with CH2Cl2 (3 ϰ 2 mL), the organic phase was treated with anhydrous Na2SO4 after filter over celite and analyzed by Gas Chromatography (GC–MS) on an Agilent 6890N GC with a 30.0 m DB-1MS capillary column coupled to an Agilent 5973 Inert Mass Selective detector. Additional experiments of catalysis were carried out under the same reaction conditions using different bases Na2CO3, K2CO3, Li2CO3, Cs2CO3, Rb2CO3, NaOH, KOH, Et3N, and DIPEA.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 42, p. 5841 - 5845
[2] Molecules, 2017, vol. 22, # 3,
[3] New Journal of Chemistry, 2017, vol. 41, # 12, p. 5105 - 5113
  • 4
  • [ 19006-82-7 ]
  • [ 39774-26-0 ]
Reference: [1] Patent: US5824624, 1998, A,
[2] Patent: US5849758, 1998, A,
  • 5
  • [ 626-05-1 ]
  • [ 591-50-4 ]
  • [ 39774-26-0 ]
Reference: [1] Patent: US5576338, 1996, A,
  • 6
  • [ 39774-25-9 ]
  • [ 39774-26-0 ]
Reference: [1] Patent: WO2006/67931, 2006, A1, . Location in patent: Page/Page column 55
[2] Journal of the American Chemical Society, 1956, vol. 78, p. 5842
  • 7
  • [ 626-05-1 ]
  • [ 603-33-8 ]
  • [ 39774-26-0 ]
Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 24, p. 5214 - 5228
  • 8
  • [ 108-86-1 ]
  • [ 440680-34-2 ]
  • [ 39774-26-0 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 50, p. 10043 - 10049
  • 9
  • [ 626-05-1 ]
  • [ 24388-23-6 ]
  • [ 39774-26-0 ]
Reference: [1] Synthetic Communications, 2005, vol. 35, # 14, p. 1897 - 1902
  • 10
  • [ 100-59-4 ]
  • [ 466635-13-2 ]
  • [ 39774-26-0 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 22, p. 4429 - 4438
  • 11
  • [ 626-05-1 ]
  • [ 39774-26-0 ]
Reference: [1] Tetrahedron, 2003, vol. 59, # 50, p. 10043 - 10049
[2] Tetrahedron, 2002, vol. 58, # 22, p. 4429 - 4438
  • 12
  • [ 76700-38-4 ]
  • [ 39774-26-0 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 22, p. 4429 - 4438
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