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[ CAS No. 3430-16-8 ] {[proInfo.proName]}

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Chemical Structure| 3430-16-8
Chemical Structure| 3430-16-8
Structure of 3430-16-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3430-16-8 ]

CAS No. :3430-16-8 MDL No. :MFCD01646141
Formula : C6H6BrN Boiling Point : -
Linear Structure Formula :- InChI Key :ADCLTLQMVAEBLB-UHFFFAOYSA-N
M.W : 172.02 Pubchem ID :817713
Synonyms :

Calculated chemistry of [ 3430-16-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.9
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 1.91
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 1.58
Log Po/w (SILICOS-IT) : 2.54
Consensus Log Po/w : 2.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.66
Solubility : 0.372 mg/ml ; 0.00216 mol/l
Class : Soluble
Log S (Ali) : -1.8
Solubility : 2.7 mg/ml ; 0.0157 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.26
Solubility : 0.0948 mg/ml ; 0.000551 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 3430-16-8 ]

Signal Word:Danger Class:N/A
Precautionary Statements:P280-P301+P312+P330-P305+P351+P338+P310 UN#:N/A
Hazard Statements:H302-H318 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3430-16-8 ]

* 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 [ 3430-16-8 ]
  • Downstream synthetic route of [ 3430-16-8 ]

[ 3430-16-8 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 3430-16-8 ]
  • [ 3430-19-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
  • 2
  • [ 3430-16-8 ]
  • [ 97674-02-7 ]
  • [ 1721-12-6 ]
YieldReaction ConditionsOperation in experiment
160 mg
Stage #1: With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 1 h; Microwave irradiation
Stage #2: With hydrogenchloride; water In methanol at 20℃;
The following are successively introduced into a microwave tube: 469.80 μl (4.07 mmol) of 3-bromo-5-methylpyridine in 20 mL of H2O/DMF: (1/3: v/v), 2.03 mL (5.70 mmol) of tributyl(1-ethoxyvinyl)tin, 57.12 mg (81 .38 mmol) of bis(triphenylphosphine)palladium(ll) chloride, 1.12 g (8.14 mmol) of potassium carbonate. After irradiating with microwaves for 1 hour at 1 10°C, the reaction mixture is evaporated to dryness and the residue is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is taken up in a solution consisting of 6 mL of methanol and 1 mL of 1 N hydrochloric acid. After stirring overnight at room temperature, the reaction mixture is evaporated to dryness and the residue is taken up in saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 160 mg of 1-(2-methylpyrid-3-yl)ethanone, the characteristics of which are as follows: LC/MS (method G): ESI+ [M+H]+: m/z 136. tr (min) = 0.38. 1H NMR (300 MHz, δ in ppm, DMSO-d6): 2.58 (s, 3H), 2.61 (s, 3H), 7.38 (m, 1 H), 8.2 (m, 1 H), 8.57 (m, 1 H).
160 mg With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 1 h; Microwave irradiation The following are successively introduced into a microwave tube:
469.80 μl (4.07 mmol) of 3-bromo-5-methylpyridine in 20 mL of H2O/DMF: (1/3: v/v), 2.03 mL (5.70 mmol) of tributyl(1-ethoxyvinyl)tin, 57.12 mg (81.38 mmol) of bis(triphenylphosphine)palladium(II) chloride, 1.12 g (8.14 mmol) of potassium carbonate.
After irradiating with microwaves for 1 hour at 110° C., the reaction mixture is evaporated to dryness and the residue is taken up in water and extracted with ethyl acetate.
The organic phase is dried over magnesium sulfate and evaporated to dryness.
The residue is taken up in a solution consisting of 6 mL of methanol and 1 mL of 1 N hydrochloric acid.
After stirring overnight at room temperature, the reaction mixture is evaporated to dryness and the residue is taken up in saturated aqueous NaHCO3 solution and extracted with ethyl acetate.
The organic phase is dried over magnesium sulfate and evaporated to dryness.
The residue is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 160 mg of 1-(2-methylpyrid-3-yl)ethanone, the characteristics of which are as follows:
LC/MS (method G): ESI+ [M+H]+: m/z 136 tr (min)=0.38
1H NMR (300 MHz, δ in ppm, DMSO-d6): 2.58 (s, 3H), 2.61 (s, 3H), 7.38 (m, 1H), 8.2 (m, 1H), 8.57 (m, 1H).
Reference: [1] Patent: WO2013/190123, 2013, A1, . Location in patent: Page/Page column 62
[2] Patent: US2015/183804, 2015, A1, . Location in patent: Paragraph 0618; 0619; 0620; 0621
  • 3
  • [ 3430-16-8 ]
  • [ 20826-04-4 ]
Reference: [1] Synthesis, 2003, # 4, p. 551 - 554
  • 4
  • [ 625-92-3 ]
  • [ 823-96-1 ]
  • [ 3430-16-8 ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate In 1,4-dioxane; water at 100 - 110℃; for 32 h; Add cesium carbonate (1. 38 g, 4. 22 mmol), trimethylboroxine (0. 2 mL, 1. 47 mmol) and tetrakis (triphenylphosphine) palladium (0) (0. 488 g, 0. 42 mmol) to a solution of 3, 5-dibromopyridine (1. 0 g, 4. 22 mmol) in 9 : 1 dioxane : water (10 mL) and stir under nitrogen at 110 °C for 16 h. Add more trimethylboroxine (0. 2 mL, 1. 47 mmol) and stir at 100 °C for an additional 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, and wash with ethyl acetate. Concentrate the filtrate and purify the residue by silica gel chromatography, eluting with 80 : 20 hexane : ethyl acetate, to give the title compound as a colorless oil (0. 654 g, 90percent). 1H NMR (300 MHz, Cd13) 8 2. 34 (s, 3 H), 7. 66 (s, 1 H), 8. 36 (s, 1 H), 8. 49 (s, 1 H). GC-MS (EI) : m/z= 171. 0, 173. 0 [M].
Reference: [1] Patent: WO2005/94822, 2005, A1, . Location in patent: Page/Page column 25
  • 5
  • [ 3430-18-0 ]
  • [ 3430-16-8 ]
YieldReaction ConditionsOperation in experiment
68% With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 0.5 h; Inert atmosphere General procedure: Pd(OAc)2-PPh3, Pd2(dba)3-tbpf, Pd2(dba)3-DavePhos Pd2(dba)3-P(t-Bu)3 Pd2(dba)3-XantPhos and Pd(OAc)2-XPhos. Anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes, then Pd(OAc)2 (7.2 mg, 0.033 mmol, 5 molpercent) and PPh3 (17.7 mg, 1.132 mmol, 20 molpercent) were added and the resulting mixture stirred at room temperature for 30 min. The halogenated heterocycle (0.66 mmol), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature or heated at 65 °C under argon for the proper time. The residue was taken up in brine and extracted with ethyl acetate. The organic phase was separated, dried, the solvent was evaporated and the residue was purified by flash chromatography (mixtures of petroleum ether and ethyl acetate) to give pure hydrodehalogenated heterocycles
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
  • 6
  • [ 3430-19-1 ]
  • [ 3430-16-8 ]
Reference: [1] Patent: CN107162963, 2017, A, . Location in patent: Paragraph 0026
  • 7
  • [ 591-22-0 ]
  • [ 3430-16-8 ]
Reference: [1] Patent: WO2007/107758, 2007, A1, . Location in patent: Page/Page column 76
  • 8
  • [ 108-99-6 ]
  • [ 3430-16-8 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 49, p. 6743 - 6746
  • 9
  • [ 3430-16-8 ]
  • [ 173999-18-3 ]
Reference: [1] Patent: WO2006/20879, 2006, A1, . Location in patent: Page/Page column 102
[2] British Journal of Pharmacology, 2018, vol. 175, # 17, p. 3470 - 3485
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