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[ CAS No. 960298-00-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 960298-00-4
Chemical Structure| 960298-00-4
Chemical Structure| 960298-00-4
Structure of 960298-00-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 960298-00-4 ]

CAS No. :960298-00-4 MDL No. :MFCD13190654
Formula : C12H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZBTZIRNIUHLSSJ-UHFFFAOYSA-N
M.W :264.12 Pubchem ID :53217389
Synonyms :

Calculated chemistry of [ 960298-00-4 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.92
TPSA : 22.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 3.27
Log Po/w (MLOGP) : 2.83
Log Po/w (SILICOS-IT) : 3.52
Consensus Log Po/w : 3.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0279 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (Ali) : -3.48
Solubility : 0.0871 mg/ml ; 0.00033 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.54
Solubility : 0.00076 mg/ml ; 0.00000288 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.11

Safety of [ 960298-00-4 ]

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

Application In Synthesis of [ 960298-00-4 ]

* 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 [ 960298-00-4 ]
  • Downstream synthetic route of [ 960298-00-4 ]

[ 960298-00-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 960298-00-4 ]
  • [ 36953-37-4 ]
YieldReaction ConditionsOperation in experiment
82% With hydrogenchloride In methanolReflux To a solution of 2-benzyloxy-4-bromopyridine 6 (201 mg, 0.8 mmol) in MeOH(4.5 mL) was added conc. HCl (2.3 mL). The mixture was heated at reflux overnight.Then the reaction mixture was cooled to room temperature and concentrated underreduced pressure. The residue was poured into cold water and carefully quenchedwith aq. sat. Na2CO3. The aqueous layer was extracted with ethyl acetate (3x). Thecombined organic layers were washed with brine, dried (Na2SO4), filtered andconcentrated under reduced pressure. The crude was purified by flash chromatography on silica gel (EtOAc/MeOH: 98/2) to give 1c (109 mg, 82percent) as acolorless solid. Data for 1c are reported above.
Reference: [1] Synlett, 2016, vol. 27, # 1, p. 67 - 69
  • 2
  • [ 128071-98-7 ]
  • [ 100-51-6 ]
  • [ 960298-00-4 ]
YieldReaction ConditionsOperation in experiment
99% With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; Inert atmosphere Example 19i2-(Benzyloxy)-4-bromopyridine4-Bromo-2-fluoropyridine (5.28 g, 30 mmol) and benzyl alcohol (3.24 g, 30.00 mmol) were dissolved in dry THF (50 mL) under an atmosphere of argon. The solution was cooled with an external ice/water bath and held at 0 0C. Potassium tert-butoxidc (3.37 g, 30.00 mmol) was added in portions (approx. 100 mg each) under efficient stirring over a period of 20 min. Stirring at 0 0C was continued for 60 min, whereafter the cooling bath was removed and the mixture was stirred at rt for 30 min. Water (5 mL) was added to the reaction mixture and most of the THF was evaporated under reduced pressure. The remaining mixture was partitioned between pentane (75 mL) and water (50 mL). The organic phase was separated, washed with water (2x25 mL), dried over MgSO4 and the solvents removed in vacuo to afford 7.86 g (99percent) of the title compound.1H NMR (500 MHz, DMSO-J6) δ 8.10 (d, IH) 7.44 (d, 2H) 7.38 (t, 2H) 7.33 (t, IH) 7.25 (d, IH) 7.20 (s, IH) 5.36 (s, 2H).
Reference: [1] Patent: WO2011/2409, 2011, A1, . Location in patent: Page/Page column 37
[2] Patent: WO2010/66028, 2010, A1, . Location in patent: Page/Page column 28-29
[3] Patent: WO2009/135299, 2009, A1, . Location in patent: Page/Page column 108
  • 3
  • [ 73583-37-6 ]
  • [ 100-51-6 ]
  • [ 960298-00-4 ]
YieldReaction ConditionsOperation in experiment
46.3%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 4 h;
Stage #2: at 0 - 25℃;
To a solution of phenylmethanol (2.248 g, 20.79 mmol) in THF (100 mL), was added NaH (60percent w/w) (0.914 g, 22.86 mmol) at 0°C. The reaction mixture was stirred at 0°C for 4 hr. 4-bromo-2- chloropyridine (2 g, 10.39 mmol) in THF (50 mL) was added dropwise into the reaction mixture at 0 °C. The reaction mixture was stirred at 25°C for overnight. The reaction mixture was partitioned between EtOAc (100 mL) and water (100 mL). The organic phase was washed with saturated brine (100 mL), dried over sodium sulphate and evaporated in vacuo to give the crude product. The crude product was purified by Combi-Flash chromatography on a silica column (24g) and eluted with EtOAc/petroleum (0-100percent over 10 min, 100percent over 5 min). Appropriate fractions were evaporated to give the title compound (1.272 g, 4.82 mmol, 46.3 percent yield) as a white oil. LCMS: MH+ =264/266
0.71 g
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; for 0.166667 h; Cooling with ice
Stage #2: for 3 h; Reflux
(1) 0.37 g of sodium hydride was added to a mixed solution comprising 1.1 g of benzyl alcohol and 3 mL of tetrahydrofuran while cooling with an ice bath, followed by stirring at room temperature for 10 minutes. A mixed solution comprising 0.60 g of 4- bromo-2-chloropyridine and 1 mL of tetrahydrofuran, was added to the reaction solution, followed by heating and refluxing for 3 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and an aqueous sodium chloride solution, and anhydrous sodium sulfate was added for drying. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n- heptane/ethyl acetate=10/1) to obtain 0.71 g of oily 2-(benzyloxy)-4-bromopyridine.
Reference: [1] Patent: WO2014/78257, 2014, A1, . Location in patent: Page/Page column 129
[2] Patent: WO2013/27660, 2013, A1, . Location in patent: Page/Page column 23
  • 4
  • [ 100-39-0 ]
  • [ 960298-00-4 ]
Reference: [1] Patent: WO2009/70869, 2009, A1, . Location in patent: Page/Page column 43; 59-60
  • 5
  • [ 36953-37-4 ]
  • [ 100-39-0 ]
  • [ 960298-00-4 ]
Reference: [1] Patent: WO2010/132601, 2010, A1, . Location in patent: Page/Page column 467
  • 6
  • [ 36953-37-4 ]
  • [ 100-39-0 ]
  • [ 960298-00-4 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 14, p. 3382 - 3385
  • 7
  • [ 14432-12-3 ]
  • [ 960298-00-4 ]
Reference: [1] Synlett, 2016, vol. 27, # 1, p. 67 - 69
  • 8
  • [ 100-51-6 ]
  • [ 960298-00-4 ]
Reference: [1] Synlett, 2016, vol. 27, # 1, p. 67 - 69
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