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[ CAS No. 1030825-20-7 ] {[proInfo.proName]}

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Chemical Structure| 1030825-20-7
Chemical Structure| 1030825-20-7
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Product Details of [ 1030825-20-7 ]

CAS No. :1030825-20-7 MDL No. :MFCD21496340
Formula : C18H14BrFS Boiling Point : -
Linear Structure Formula :- InChI Key :VLRIERSBZHUCOW-UHFFFAOYSA-N
M.W : 361.27 Pubchem ID :46930432
Synonyms :

Calculated chemistry of [ 1030825-20-7 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.11
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 91.83
TPSA : 28.24 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.81
Log Po/w (XLOGP3) : 6.38
Log Po/w (WLOGP) : 6.64
Log Po/w (MLOGP) : 5.81
Log Po/w (SILICOS-IT) : 7.68
Consensus Log Po/w : 6.06

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.5
Solubility : 0.000114 mg/ml ; 0.000000316 mol/l
Class : Poorly soluble
Log S (Ali) : -6.76
Solubility : 0.0000621 mg/ml ; 0.000000172 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.58
Solubility : 0.000000959 mg/ml ; 0.0000000026 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.93

Safety of [ 1030825-20-7 ]

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 [ 1030825-20-7 ]

* 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 [ 1030825-20-7 ]
  • Downstream synthetic route of [ 1030825-20-7 ]

[ 1030825-20-7 ] Synthesis Path-Upstream   1~16

  • 1
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YieldReaction ConditionsOperation in experiment
97.7% With borane-THF In tetrahydrofuran at -20 - -10℃; for 48 h; 15 g (5-bromo-2-methylphenyl)[5-(p-fluorophe- nyl)thiophene-2-yl]methanone was weighed and dissolved in 150 ml tetrahydroffiran, and 30 ml of 1 M boranetetrahydroffiran complex was added. The system was reacted at —20° C. to —10° C. for 48 hours. After the complete reaction of raw materials, 30 ml water was added. The mixture was extracted with 100 ml dichloromethane, and then the extract was concentrated to give 14.25 g of 2-(2-methyl-5-bromobenzyl)-5-(4-fluorophenyl)thiophene, with a purity of 98.9percent and in a yield of 97.7percent
84% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 35℃; 56.5 g of (5-bromo-2-methylphenyl)[2-(4-fluorophenyl)thiophene]methanone to be prepared according to Example 5. Dissolve (0.44 mol) in 600 ml of dichloromethane-acetonitrile (1:1, v/v), cool to 0°C in an ice water bath, and add dropwise triethylsilane.100 ml (0.63 mol), and then slowly added 47percent boron trifluoride ether 42 ml (0.33 mol), slowly added to the 20-The reaction was stirred at 35° C. for 4 hours. After the TLC reaction was completed, it was quenched with a saturated light carbonic acid solution and extracted with dichloromethane.The organic phase was washed with water and saturated brine, and the solvent was evaporated under reduced pressure. The residue was re-constituted with dichloromethane-methanol (1:1, v/v). Crystalline 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene, 13.3 g, yield 84percent
70% With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 20℃; for 3 h; Synthesis of compound 44Ci8Hi4BrFS M = 361.27 g.mol"1 19FNMR (CDCh, 282.5MHz): -115.0 (m, IF, Ar-F).Mass ESf): 133 (29percent); 177 (49percent); 182 (55percent); 184 (70percent); 191 (72percent); 281 (39percent); 360 (95percent); 362 (100percent)F Et3SiH DCM/MeCN Et3SiH (0.99mL, 6.18mmol, 2.9eq) was added at room temperature to a solution of ketone 43 (800mg, 2.13mmol, leq) in anhydrous dichloromethane-acetonitrile (1 :1, v/v, 16mL). The resultant mixture was cooled to 0°C and BF3.Et20 (0.75mL, 5.97mmol, 2.8eq) was slowly added. The reaction mixture was then stirred at room temperature for 3 hours. A saturated aqueous solution of NaHC03 was slowly added at 0°C. The aqueous layer was extracted with dichloromethane and the resultant organic layer was dried over MgS04, filtered and concentrated. The crude mixture was then recristallized with MeOH to afford compound 44 (70percent yield) as yellowish crystals.
3.65 g With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 20℃; for 26 h; 2-(5-Bromo-2-methyl-benzoyl)-5-(4-fluoro-phenyl)-phenyl)-thiophene (8, 3.75 g) was dissolved in dichloromethane (40 ml) and acetonitrile (40 ml), to which triethylsilane (4.63 ml) was added and cooled to 0 °C. Boron trifluoride etherate (3.45 ml) was added to the suspension and the reaction mixture was left to warm up to room temperature then continued to stir at that temperature for 26 h. The reaction mixture was cooled on ice and 50 ml of NaHCO3 was slowly added, followed by adding dichloromethane (50 ml). Phases were separated and organic phase was dried over sulphate, and then evaporated. The residue was recrystallized from 2-propanol to give 3.65 g of the title compound 1a. 13C NMR (DMSO): 18.52, 32.84, 115.83, 116.00, 118.81, 123.52, 126.86, 126.99, 127.05, 129.50, 130.41, 131.60, 132.37, 135.54, 140.63, 141.16, 142.46, 160.48, 162.42. MS, m/z= 360.

Reference: [1] Patent: US2017/44129, 2017, A1, . Location in patent: Paragraph 0013-0024
[2] Patent: CN107556287, 2018, A, . Location in patent: Paragraph 0057; 0058; 0059
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 17, p. 6355 - 6360
[4] Patent: WO2012/160218, 2012, A1, . Location in patent: Page/Page column 72-73
[5] Patent: WO2009/35969, 2009, A1, . Location in patent: Page/Page column 76-77
[6] Patent: EP2918579, 2015, A1, . Location in patent: Paragraph 0045; 0046
[7] Patent: WO2016/16852, 2016, A1, . Location in patent: Page/Page column 7; 8
  • 2
  • [ 58861-48-6 ]
  • [ 87604-18-0 ]
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YieldReaction ConditionsOperation in experiment
78% With zinc(II) chloride In ethyl acetate for 6 h; Reflux; Large scale Take 2-methyl-5-bromobenzyl chloride 110kg,Dissolved in 250kg of ethyl acetate,80kg of 2-p-fluorophenylthiophene was added,Zinc chloride 70kg,Heated to reflux reaction 6h,After the reaction was completed, the mixture was cooled to room temperature, 400 kg of water was added, extracted, and 200 kg of water was washed with anhydrous sulfurSodium soda, filtration, the filtrate recovery 100kg, crystallization was light yellow crystals 141kg, a yield of 78percent.
Reference: [1] Patent: CN107011316, 2017, A, . Location in patent: Paragraph 0006; 0013; 0015
  • 3
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Reference: [1] Patent: WO2012/160218, 2012, A1,
[2] Patent: EP2918579, 2015, A1,
  • 4
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Reference: [1] Patent: WO2012/160218, 2012, A1,
  • 5
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Reference: [1] Patent: WO2012/160218, 2012, A1,
[2] Patent: WO2016/16852, 2016, A1,
[3] Patent: CN107556287, 2018, A,
  • 6
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Reference: [1] Patent: WO2012/160218, 2012, A1,
  • 7
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Reference: [1] Patent: EP2918579, 2015, A1,
  • 8
  • [ 918487-45-3 ]
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Reference: [1] Patent: EP2918579, 2015, A1,
  • 9
  • [ 98-03-3 ]
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Reference: [1] Patent: EP2918579, 2015, A1,
  • 10
  • [ 249504-38-9 ]
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Reference: [1] Patent: EP2918579, 2015, A1,
  • 11
  • [ 1765-93-1 ]
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Reference: [1] Patent: WO2016/16852, 2016, A1,
  • 12
  • [ 64688-68-2 ]
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Reference: [1] Patent: CN104311532, 2016, B,
  • 13
  • [ 90050-59-2 ]
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Reference: [1] Patent: CN104072348, 2018, B,
  • 14
  • [ 462-06-6 ]
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Reference: [1] Patent: CN107556287, 2018, A,
  • 15
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Reference: [1] Patent: CN107556287, 2018, A,
  • 16
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  • [ 898566-17-1 ]
YieldReaction ConditionsOperation in experiment
94.9 g With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene for 36 h; Inert atmosphere; Reflux 10098] 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene (100 g; see WO 2005/012326 pamphlet) was dissolved in toluene (300 mL) at room temperature under N2 atmosphere. Sodium iodide (83 g), copper (I) iodide (2.64 g), N,N’-dimethyl ethylenediamine (2.94 mL) and diglyme (50 mL) was added to the mixture at room temperature. The reaction mixture was heated to reflux temperature and stirred for 36 hours. Ethyl acetate (300 mL) was added to the mixture at 40° C. and the mixture was filtered using activated carbon pre-coated filtet The filtrate was washed and then evaporated. The resulting residue was suspended in methanol (426 mL) at reflux temperature for 75 minutes. The resulting slurry was cooled to 25° C. and stirred for 1 hout The precipitate was filtered and washed with methanol, then dried at 50° C. in vacuo to give 2-(5-iodo-2-methylbenzyl)-5-(4-fluorophenyl) thiophene (94.9 g) as white crystals. mlz (APCI), 409 (M+ H);mp 109-110° C.
Reference: [1] Patent: WO2009/35969, 2009, A1, . Location in patent: Page/Page column 77
[2] Patent: US2010/99883, 2010, A1, . Location in patent: Page/Page column 43
[3] Patent: US2016/228375, 2016, A1, . Location in patent: Paragraph 0097; 0098
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