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[ CAS No. 4595-60-2 ] {[proInfo.proName]}

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Chemical Structure| 4595-60-2
Chemical Structure| 4595-60-2
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Product Details of [ 4595-60-2 ]

CAS No. :4595-60-2 MDL No. :MFCD00014601
Formula : C4H3BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :PGFIHORVILKHIA-UHFFFAOYSA-N
M.W : 158.98 Pubchem ID :78345
Synonyms :

Calculated chemistry of [ 4595-60-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.73
TPSA : 25.78 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) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 0.5
Log Po/w (WLOGP) : 1.24
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.08

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.77
Solubility : 2.67 mg/ml ; 0.0168 mol/l
Class : Very soluble
Log S (Ali) : -0.61
Solubility : 38.9 mg/ml ; 0.245 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.512 mg/ml ; 0.00322 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.53

Safety of [ 4595-60-2 ]

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

Application In Synthesis of [ 4595-60-2 ]

* 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 [ 4595-60-2 ]
  • Downstream synthetic route of [ 4595-60-2 ]

[ 4595-60-2 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 867-44-7 ]
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  • [ 823-09-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6316 - 6321
  • 2
  • [ 4595-60-2 ]
  • [ 5188-07-8 ]
  • [ 823-09-6 ]
Reference: [1] Tetrahedron, 2002, vol. 58, # 5, p. 887 - 890
  • 3
  • [ 773837-37-9 ]
  • [ 4595-60-2 ]
  • [ 14080-23-0 ]
Reference: [1] Patent: US2003/229079, 2003, A1, . Location in patent: Page 40
  • 4
  • [ 4595-60-2 ]
  • [ 98-80-6 ]
  • [ 7431-45-0 ]
YieldReaction ConditionsOperation in experiment
79% With potassium phosphate In ethanol; water at 100℃; for 8 h; General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100°C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis.
69% With C32H26NO2PPdS; potassium carbonate In ethanol; N,N-dimethyl acetamide; water at 100℃; for 12 h; General procedure: To the catalyst (1.0 molpercent) dissolved in 1 ml DMAc, aryl bromide (1.0 mmol), phenyl boronic acid (1.5 mmol) in 1 ml ethanol, K2CO3 (2.0 mmol) in 1 ml water and DMAc (5 ml) were all added. The mixture was heated at 100 °C for 12 h. Then, the mixture was cooled, water was added and the product was extracted with ethylacetate. The organic layer was washed with brine, dried over Na2SO4, filtered, passed through celite, and analyzed by GC. Yields were based on corresponding aryl bromides.
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4455 - 4458
[2] Tetrahedron, 2005, vol. 61, # 51, p. 12121 - 12130
[3] Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3255 - 3266
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 27, p. 5901 - 5905
[5] Inorganica Chimica Acta, 2018, vol. 477, p. 227 - 232
[6] Inorganica Chimica Acta, 2013, vol. 394, p. 391 - 400
[7] Journal of Materials Chemistry A, 2014, vol. 2, # 38, p. 15945 - 15951
[8] European Journal of Organic Chemistry, 2011, # 19, p. 3474 - 3481
[9] Journal of Organometallic Chemistry, 2002, vol. 663, # 1-2, p. 46 - 57
[10] Journal of the American Chemical Society, 2010, vol. 132, # 30, p. 10272 - 10274
[11] Organic Letters, 2014, vol. 16, # 7, p. 2046 - 2049
[12] Organic Letters, 2015, vol. 17, # 3, p. 660 - 663
[13] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516
[14] Angewandte Chemie - International Edition, 2015, vol. 54, # 15, p. 4508 - 4511[15] Angew. Chem., 2015, vol. 127, # 15, p. 4591 - 4594,4
[16] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3716 - 3731
  • 5
  • [ 143-66-8 ]
  • [ 4595-60-2 ]
  • [ 7431-45-0 ]
Reference: [1] Chemical Communications, 2009, # 42, p. 6430 - 6432
  • 6
  • [ 109674-45-5 ]
  • [ 4595-60-2 ]
  • [ 7431-45-0 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 68, p. 36262 - 36266
  • 7
  • [ 110-91-8 ]
  • [ 4595-60-2 ]
  • [ 57356-66-8 ]
Reference: [1] ChemSusChem, 2013, vol. 6, # 8, p. 1455 - 1460
  • 8
  • [ 110-91-8 ]
  • [ 201230-82-2 ]
  • [ 4595-60-2 ]
  • [ 562101-40-0 ]
  • [ 57356-66-8 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 16, p. 4296 - 4299
  • 9
  • [ 1722-12-9 ]
  • [ 4595-60-2 ]
Reference: [1] European Journal of Organic Chemistry, 2002, # 24, p. 4181 - 4184
[2] Tetrahedron Letters, 2000, vol. 41, # 10, p. 1653 - 1656
  • 10
  • [ 109-12-6 ]
  • [ 4595-60-2 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
  • 11
  • [ 4595-60-2 ]
  • [ 34671-83-5 ]
Reference: [1] Tetrahedron, 1994, vol. 50, # 41, p. 11893 - 11902
[2] Journal of the American Chemical Society, 1980, vol. 102, # 2, p. 611 - 620
  • 12
  • [ 4595-60-2 ]
  • [ 3921-01-5 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 12, p. 2497 - 2500
  • 13
  • [ 81290-20-2 ]
  • [ 4595-60-2 ]
  • [ 116470-67-8 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With silver fluoride In N,N-dimethyl-formamide at 20℃; for 0.333333 h;
Stage #2: With copper In N,N-dimethyl-formamide for 4 h;
Stage #3: at 20℃; for 12 h;
General procedure: To a well stirred mixture of AgF (1.27 g, 10 mmol) in 10 ml of DMF, Me3SiCF3 (1.7 g, 12 mmol) was added at room temperature. The mixture was stirred for 20 min and copper powder (1.0 g, 15 mmol) was added. After stirring for 4 h, the formation of CuCF3 was complete. The corresponding halogen containing compound (9 mmol) (in the case of 2,6-dibromopyridine, 4.5 mmol) was added and the reaction mixture was stirred under conditions surveyed in Table 1. The reaction was terminated unless signals of CuCF3 were no longer detected in the 19F NMR spectra. The mixture was filtered from the solid precipitate and poured into 50 ml of water. The organic layer was extracted with diethyl ether and dried over MgSO4. Ether was evaporated and the remainder was distilled under reduced pressure or crystallized.
Reference: [1] Journal of Fluorine Chemistry, 2012, vol. 133, p. 67 - 71
  • 14
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  • [ 116470-67-8 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 6, p. 2075 - 2084
  • 15
  • [ 4595-60-2 ]
  • [ 116470-67-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 79, p. 75465 - 75469
  • 16
  • [ 2923-18-4 ]
  • [ 4595-60-2 ]
  • [ 116470-67-8 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 5, p. 2676 - 2699
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 921 - 926
  • 17
  • [ 4595-60-2 ]
  • [ 116470-67-8 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 6, p. 1744 - 1747
  • 18
  • [ 77152-08-0 ]
  • [ 4595-60-2 ]
  • [ 116470-67-8 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11126 - 11146
  • 19
  • [ 4595-60-2 ]
  • [ 116470-67-8 ]
Reference: [1] Science, 2018, vol. 360, # 6392, p. 1010 - 1014
  • 20
  • [ 4595-60-2 ]
  • [ 115-19-5 ]
  • [ 37972-24-0 ]
Reference: [1] European Journal of Organic Chemistry, 2005, # 3, p. 522 - 531
  • 21
  • [ 4595-60-2 ]
  • [ 1066-54-2 ]
  • [ 37972-24-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2185 - 2191
  • 22
  • [ 87199-17-5 ]
  • [ 4595-60-2 ]
  • [ 77232-38-3 ]
Reference: [1] Patent: WO2004/65394, 2004, A1, . Location in patent: Page 49
[2] Patent: US2005/203086, 2005, A1, . Location in patent: Page/Page column 48
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
  • 23
  • [ 4226-01-1 ]
  • [ 4595-60-2 ]
  • [ 153435-63-3 ]
Reference: [1] Patent: US2004/110785, 2004, A1, . Location in patent: Page 101; 105
  • 24
  • [ 123-75-1 ]
  • [ 4595-60-2 ]
  • [ 192197-34-5 ]
Reference: [1] ChemSusChem, 2013, vol. 6, # 8, p. 1455 - 1460
  • 25
  • [ 25487-66-5 ]
  • [ 4595-60-2 ]
  • [ 579476-26-9 ]
Reference: [1] Synlett, 2000, # 6, p. 829 - 831
  • 26
  • [ 14047-29-1 ]
  • [ 4595-60-2 ]
  • [ 199678-12-1 ]
YieldReaction ConditionsOperation in experiment
89% With sodium carbonate In acetonitrile at 90℃; for 17 h; Example 105 N-(PYRIDIN-3-YLMETHYL)-10-(4-PYRIMIDIN-2-YLBENZOYL)-10,11-DIHYDRO-5H-PYRROLO[2,1-C][1,4]BENZODIAZEPINE-3-CARBOXAMIDE Step A. 4-Pyrimidin-2-ylbenzoic acid; To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 2-bromopyrimidine (0.630 g, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and the mixture was purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (240 mg) was then added and the reaction mixture heated to 90° C. for 17 hours. The hot reaction mixture was filtered through celite and concentrated in vacuo to remove the acetonitrile. The resulting aqueous suspension was washed with dichloromethane (2.x.30 mL) and then acidified to pH 1 by the addition of concentrated hydrochloric acid. The resulting white suspension was diluted with water (20 mL), filtered and the solid product dried in vacuo at 50° C. overnight to give the title compound (0.709 g, 89percent) as a white solid, m.p. 237° C. MS [(+)ESI, m/z]: 201 [M+H]+ MS [(-)ESI, m/z]: 199 [M-H]- Anal. Calcd for C11H8N2O2: C, 66.00; H, 4.03; N, 13.99. Found: C, 65.72; H, 3.87; N, 14.01.
2 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In acetonitrileInert atmosphere; Reflux To a solution of compound 1 (2g, 12.6mmol) and compound 2 (2.2g, 13.2mmol) in CH3CN, was added 0.5M Na2CO3 (2.7g, 25.2mmol) and the mixture was purged with N2 for 10 mm. Pd(PPh3)4 (800mg) was then added and the mixture heated at reflux overnight. The mixture was filtered, diluted with water and extracted with EA. The resulting aqueous mixture was acidified to pH = 1 and a precipitate formed. The precipitate was filtered and dried to give 2g of compound 3.
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8670 - 8692
[2] Patent: US2006/287522, 2006, A1, . Location in patent: Page/Page column 51
[3] Synlett, 2000, # 6, p. 829 - 831
[4] Patent: WO2016/77232, 2016, A2, . Location in patent: Page/Page column 44; 45
  • 27
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  • [ 885702-33-0 ]
Reference: [1] Synthesis, 2008, # 22, p. 3697 - 3702
  • 28
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  • [ 223463-14-7 ]
  • [ 942189-65-3 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In methanol; water; tolueneHeating / reflux A mixture of 2-bromopyrimidine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylpnosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSd, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25percent v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 85percent) ESMS (MH, 236).
5% With caesium carbonate In methanol; water; tolueneHeating / reflux A mixture of 2-bromopyridine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylphosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSO4,filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25percent v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 5percent) ESMS (MH, 236).
Reference: [1] Patent: WO2007/70398, 2007, A1, . Location in patent: Page/Page column 226
[2] Patent: WO2008/156739, 2008, A1, . Location in patent: Page/Page column 210-211
[3] Patent: WO2007/97937, 2007, A1, . Location in patent: Page/Page column 183
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