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[ CAS No. 3466-32-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3466-32-8
Chemical Structure| 3466-32-8
Chemical Structure| 3466-32-8
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Product Details of [ 3466-32-8 ]

CAS No. :3466-32-8 MDL No. :MFCD00025065
Formula : C7H7BrO2S Boiling Point : -
Linear Structure Formula :- InChI Key :FJLFSYRGFJDJMQ-UHFFFAOYSA-N
M.W : 235.10 Pubchem ID :77014
Synonyms :

Calculated chemistry of [ 3466-32-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.24
TPSA : 42.52 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) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 1.25
Log Po/w (WLOGP) : 2.93
Log Po/w (MLOGP) : 2.28
Log Po/w (SILICOS-IT) : 1.8
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.42
Solubility : 0.888 mg/ml ; 0.00378 mol/l
Class : Soluble
Log S (Ali) : -1.74
Solubility : 4.27 mg/ml ; 0.0181 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.57
Solubility : 0.0634 mg/ml ; 0.00027 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 3466-32-8 ]

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 [ 3466-32-8 ]

* 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 [ 3466-32-8 ]
  • Downstream synthetic route of [ 3466-32-8 ]

[ 3466-32-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 288-47-1 ]
  • [ 3466-32-8 ]
  • [ 3704-41-4 ]
Reference: [1] Chemical Science, 2013, vol. 5, # 1, p. 123 - 135
  • 2
  • [ 3466-32-8 ]
  • [ 701-34-8 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 39, p. 7201 - 7204
  • 3
  • [ 3466-32-8 ]
  • [ 17852-67-4 ]
Reference: [1] Chinese Journal of Chemistry, 2018, vol. 36, # 11, p. 1003 - 1006
  • 4
  • [ 3466-32-8 ]
  • [ 340771-31-5 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1992, vol. 217, p. 19 - 24
[2] ChemPlusChem, 2015, vol. 80, # 6, p. 938 - 943
[3] Journal of Organic Chemistry, 2015, vol. 80, # 21, p. 10939 - 10954
[4] Green Chemistry, 2016, vol. 18, # 4, p. 932 - 936
[5] MedChemComm, 2018, vol. 9, # 3, p. 534 - 544
  • 5
  • [ 36357-38-7 ]
  • [ 3466-32-8 ]
  • [ 221615-75-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium phosphate In 1-methyl-pyrrolidin-2-one at 100℃; for 18 h; Inert atmosphere Pd(acac)2 (6.1 mg, 0.02 mmol, 0.5 mol percent) and Xantphos (23.2 mg, 0.04 mmol, 1 mol o) are introduced into a flared flask provided with coolant. 4-bromophenylmethylsulfone of formula (III, XBr) (1.17 g, 5 mmol), acetylpicoline of formula (II) (541 mg, 4 mmol) and K3PO4 (2.55 g, 12.0 mmol, 3 eq) are added thereto. Once the argon atmosphere has been stabilized with vacuum-argon cycles, anhydrous and degassed NMP (15 ml) is added with a syringe. The mixture is then kept stirred under stirring in an argon atmosphere for 18 h at 100° C. The conversion is quantitative. The reaction mixture is diluted with a saturated solution of NaHCO3 (50 mL) and extracted with AcOEt (4.x.50 mL). The combined organic phases were washed with an aqueous solution saturated with NaHCO3 (30 mL), anhydrified on MgSO4 and concentrated in a vacuum. The residue was purified by silica gel chromatography using AcOEt/cyclohexane as eluent in a gradient from 5:5 to 10:0. 1.05 g product were obtained, for a molar yield of 91percent as a white crystalline solid.
75% With tris-(dibenzylideneacetone)dipalladium(0); [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; sodium t-butanolate In toluene for 5 h; Inert atmosphere; Reflux Xantphos 0.00267 g (0.0046 mmol) and Pd2(dba)3 0.00177 g (0.0031 mmol) in 15 ml of anhydrous toluene were charged in a reactor under inert atmosphere. 4-bromophenyl methyl sulfone 0.724 g (3.078 mmol) and 3-acetyl-6-methyl pyridine 0.416 g (3.079 mmol) were then added. The mixture was heated to reflux and a suspension of t-BuONa 0.71 g in 15 ml of anhydrous toluene was added dropwise over about 4 h. After about 1 h from completion of the addition, the reaction mixture was cooled to 20 °C and a solution of diluted hydrochloric acid to acidic pH was added. The aqueous phase was separated and added dropwise over 1 h to a mixture of water 8.3 g, ethyl acetate 15.3 g and sodium bicarbonate 2.1 g at 60 °C. At addition completed and after maintaining the temperature at 60 °C for 1 h, it was checked that the pH was between 4 and 7, the mixture was cooled to 20 °C filtered and dried under vacuum at 50 °C. 0.67 g of the compound of formula 1 was obtained with a yield of 75 percent.
75% With tris-(dibenzylideneacetone)dipalladium(0); [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; sodium t-butanolate In toluene for 4 h; Inert atmosphere; Reflux Xantphos 0.00267 g (0.0046 mmol) and Pd2(dba)3 0.00177 g (0.0031 mmol) in 15 ml of anhydrous toluene were charged in a reactor under inert atmosphere. 4-bromophenyl methyl sulfone 0.724 g (3.078 mmol) and 3-acetyl-6-methyl pyridine 0.416 g (3.079 mmol) were then added. The mixture was heated to reflux and a suspension of t-BuONa 0.71 g in 15 ml of anhydrous toluene was added dropwise over about 4 h. After about 1 h from completion of the addition, the reaction mixture was cooled to 20°C and a solution of diluted hydrochloric acid to acidic pH was added. The aqueous phase was separated and added dropwise over 1 h to a mixture of water 8.3 g, ethyl acetate 15.3 g and sodium bicarbonate 2.1 g at 60°C. At addition completed and after maintaining the temperature at 60°C for 1 h, it was checked that the pH was between 4 and 7, the mixture was cooled to 20°C filtered and dried under vacuum at 50 °C. 0.67 g of the compound of formula 1 was obtained with a yield of 75 percent.
72% With tris-(dibenzylideneacetone)dipalladium(0); [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; sodium t-butanolate In toluene for 5 h; Inert atmosphere; Reflux EXAMPLE 1 [0068] Synthesis of 1-(6-methylpyridin-3-yl)-2-[(4-methylsulfonyl)-phenyl]-ethanone. [0069] Xantphos 0.027 g (0.0477 mmol) and Pd2(dba)3 0.0182 g (0.0198 mmol) in 100 ml of anhydrous toluene were charged in a reactor under inert atmosphere. 4-bromophenyl methyl sulfone 9.3 g (39.7 mmol) and 3-acetyl-6-methyl pyridine 5.4 g (39.7 mmol) were then added. The mixture was heated to reflux and a suspension of t-BuONa 8.4 g in 100 ml of anhydrous toluene was added dropwise over about 4 h. After about 1 h from completion of the addition, the reaction mixture was cooled to 20° C. and a solution of diluted hydrochloric acid to acidic pH was added. The aqueous phase was separated and added dropwise over 1 h to a mixture of water 83.3 g, ethyl acetate 153 g and sodium bicarbonate 20.1 g at 60° C. At addition completed and after maintaining the temperature at 60° C. for 1 h, it was checked that the pH was between 4 and 7, the mixture was cooled to 20° C., filtered, and dried under vacuum at 50° C. 8.3 g of the compound of formula 1 were obtained with a yield of 72percent.

Reference: [1] Patent: US2012/232281, 2012, A1, . Location in patent: Page/Page column 7-8
[2] Patent: WO2013/135587, 2013, A1, . Location in patent: Page/Page column 9; 10
[3] Patent: EP2639221, 2013, A1, . Location in patent: Paragraph 0067
[4] Patent: US2015/133671, 2015, A1, . Location in patent: Paragraph 0068; 0069
[5] Patent: EP2497767, 2012, A1, . Location in patent: Page/Page column 8-9
[6] RSC Advances, 2013, vol. 3, # 40, p. 18544 - 18549
[7] Patent: EP2757095, 2014, A1, . Location in patent: Paragraph 0048-0052
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