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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 ]      Expand+

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 ?2

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.

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

[ 1030825-20-7 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 1030825-20-7 ]
  • [ 32469-28-6 ]
  • [ 1030825-21-8 ]
YieldReaction ConditionsOperation in experiment
93.7% This embodiment is a method for preparing a cardinol intermediate, and the preparation method comprises the following steps:1) Under the protection of nitrogen,100 g (0.245 mol) of <strong>[1030825-20-7]2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene</strong> was sufficiently dissolved in 300 mL of tetrahydrofuran.At a temperature of -25 ° C to -20 ° C,100 g (0.245 mol) of sec-butylmagnesium chloride. Lithium chloride was added dropwise.After the addition was completed, the reaction was continued for 1 hour;Maintain temperature,Further, 171.6 g (0.368 mol) of 2,3,4,6-tetra-O-(trimethylsilyl)-D-gluconolactone was added dropwise.After the addition is completed,Continue to react for 2 hours;Wherein 2,3,4,6-tetra-O-(trimethylsilyl)-D-gluconolactone is previously dissolved in 200 mL of tetrahydrofuran;2) in the reaction liquid after the reaction in the step 1),51.8 g (0.539 mol) of methanesulfonic acid in methanol was added dropwise.Stir,After natural temperature reaction for 18 hours, at a temperature of -5 ° C to 5 ° C,The reaction was quenched with saturated aqueous sodium bicarbonate;3) adjusting the pH of the reaction solution after the reaction in step 2) with a saturated aqueous solution of sodium hydrogencarbonate to 7-8, and after removing the solvent under reduced pressure,Extracted with methyl n-butyl ether twice,Combine the organic phase,Dissolve the solvent under reduced pressure,Obtaining a yellow viscous solid crude;Add the crude product to 300 mL of methyl n-butyl ether.After fully dissolving, add 600 mL of n-heptane, stir, and precipitate a solid.The solvent was removed and dried under vacuum to obtain the intermediate of cagliflozin; 108.9 g of pale yellow solid was obtained, purity 87.9percent.The yield was 93.7percent.
(1) To a solution of <strong>[1030825-20-7]5-bromo-1-[5-(4-fluorophenyl)-2-thienylmethyl]-2-methylbenzene</strong> (1, 28.9 g) in tetrahydrofuran (480 ml) and toluene (480 ml) was added n-butyllithium (1.6M hexane solution, 50.0 ml) dropwise at -67 to -70 C. under argon atmosphere, and the mixture was stirred for 20 minutes at the same temperature. Thereto was added a solution of 2 (34.0 g) in toluene (240 ml) dropwise at the same temperature, and the mixture was further stirred for 1 hour at the same temperature. Subsequently, thereto was added a solution of methanesulfonic acid (21.0 g) in methanol (480 ml) dropwise, and the resulting mixture was allowed to warm to room temperature and stirred for 17 hours. The mixture was cooled under ice-water cooling, and thereto was added a saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate, and the combined organic layer was washed with brine and dried over magnesium sulfate. The insoluble was filtered off and the solvent was evaporated under reduced pressure. The residue was triturated with toluene (100 ml)-hexane (400 ml) to give 1-(1-methoxyglucopyranosyl)-4-methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]-benzene (3) (31.6 g). APCI-Mass m/Z 492 (M+NH4).
  • 2
  • [ 1030825-20-7 ]
  • [ 898566-17-1 ]
YieldReaction ConditionsOperation in experiment
With sodium iodide; N,N`-dimethylethylenediamine;copper(l) iodide; In diethylene glycol dimethyl ether; toluene; at 110℃; Example 3; 2-(4-Fluoro-phenyl)-5-(5-iodo-2-methyl-benzyl)-thiopheneA 1.0 L four-necked reaction flask was charged with the compound prepared as in Example 2 above (100 g, 276.80 mmoles), sodium Iodide (82 g, 553.59 mmoles) and Copper(l) Iodide (2.6 g, 13.84 mmoles). The resulting mixture was evacuated and purged with argon, then treated with toluene (261 ml_), diglyme (56 ml_) and N,N'-dimethyl-ethane-1 ,2-diamine (2.7 ml_, 27.68 mmoles) and the resulting mixture warmed to 11 O0C overnight. Upon consumption of starting material, the resulting mixture was cooled to room temperature, then filtered through Celite.(R)., washed with EtOAc, and extracted with NH4OH. The organic phase was dried (Na2SO4), filtered and concentrated to yield a solid. The solids were filtered and recrystallized from heptane to yield the title compound as an off white solid (m.p. 1070C). (See also, Klaper, A., Buchwald, S. L., "Copper-Catalyzed HalogenExchange in Aryl Halides: An Aromatic Finkelstein Reaction", J. Am. Chem. Soc, 2002, 124, 14844-14814)
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine; In diethylene glycol dimethyl ether; toluene; at 20℃;Inert atmosphere; Reflux; Example 15; 2-(4-fluorophenyl)-5(5-iodo-2-methylbenzyl)thiophene 2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene (100 g); (see Nomura S., et al., PCT Publication, WO 2005/012326 A1, published Feb. 10, 2005) 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 filter. The filtrate was washed twice with 5percent aqueous NH3 solution (100 mL). The organic layer was washed with water (100 mL) 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 hour. 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.m/z (APCI), 409(M++H); mp 109-110° C.; 1H NMR (400 MHz, CDCl3); delta 7.54 (d, 4JHH=1.8 Hz, 1H), 7.45-7.42 (m, 3H), 7.07-6.99 (m, 3H), 6.92 (d, 3JHH=6.0 Hz, 1H), 6.66 (d, 3JHH=3.6 Hz, 1H), 4.05 (s, 2H), 2.26 (s, 3H).
94.9 g With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine; In diethylene glycol dimethyl ether; toluene; for 36h;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.
  • 3
  • [ 1132832-75-7 ]
  • [ 1030825-20-7 ]
YieldReaction ConditionsOperation in experiment
97.7% With borane-THF; In tetrahydrofuran; at -20 - -10℃; for 48h; 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 3h; 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.
With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at -8 - 20℃; Example 2; 2-(5-Bromo-2-methyl-benzyl)-5-(4-fluoro-phenyl)-thiopheneA 3.0 L four-necked round bottom flask was charged with the compound prepared as in Example 1 above (119 g, 0.317 mol), triethylsilane (148 ml_,0.926 mol), dichloromethane (700 ml_) and acetonitrile (700 ml_). The resulting mixture was cooled to -80C in an ice bath, with stirring, then boron thfluohde diethyl etherate (115 ml_, 0.915 mol) was added dropwise, such that the temperature did not exceed O0C. The resulting mixture was warmed to room <n="79"/>temperature and stirred overnight. The resulting mixture was concentrated under reduced pressure, diluted with IPA (1.0 L), filtered and washed with water to yield a solid. Recrystallization of the solid from IPA yielded the title compound as a yellow solid.
3.65 g With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at 0 - 20℃; for 26h; 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.
With aluminum (III) chloride; sodium tetrahydroborate; In 1,2-dimethoxyethane; at 0 - 70℃; Aluminum chloride (46.12 g) was added to 1,2-dimethoxyethane (260 mL) at 0°C to 5°C. The reaction mixture was stirred for 30 minutes to 40 minutes at 5°C to 10°C. Sodium borohydride (26.19 g) was slowly added to the reaction mixture at 5°C to 10°C. The reaction mixture was stirred for 25 minutes to 30 minutes at the same temperature. A solution of (5-bromo-2-methylphenyl)[5-(4-fluorophenyl)thiophen-2-yl]methanone (130 g; Example 2) in 1,2-dimethoxyethane (260 mL) was added slowly to the reaction mixture, and then the mixture was stirred for 60 minutes at 15°C to 20°C. The reaction mixture was heated to a temperature of 65 °C to 70°C, and then stirred for 5 hours to 6 hours at the same temperature. After completion of the reaction, the reaction mixture was cooled to a temperature of 0°C to 5°C, and then added to pre-cooled de-ionized water (1300 mL) at 0°C to 10°C. The reaction mixture was stirred for 10 minutes to 15 minutes at the same temperature. Ethyl acetate (1300 mL) was added to the reaction mixture, and then the mixture was stirred for 10 to 15 minutes at 25°C to 30°C. The reaction mixture was allowed to settle for 15 minutes and then the layers were separated. The aqueous layer was washed with ethyl acetate (260 mL) and the organic layer was separated. The organic layers were combined, and then washed with an aqueous solution of sodium bicarbonate (32.5 g of sodium bicarbonate in 650 mL of de-ionized water). The organic layer was then washed with de-ionized water (260 mL). The organic layer was concentrated under reduced pressure at a temperature of about 45°C to obtain a solid residue. Methanol (390 mL) was added to the solid residue, and then the mixture was stirred for 60 minutes to 120 minutes at 0°C to 5°C to obtain a solid. The solid was washed with methanol (130 mL), and then dried under reduced pressure at 40°C to 45 °C to obtain 2-(5-bromo-2- methylbenzyl)-5 -(4-fluorophenyl)thiophene . Yield: 93percent

  • 4
  • [ 1030825-20-7 ]
  • [ 32469-28-6 ]
  • C36H57FO6SSi4 [ No CAS ]
  • 5
  • [ 460-00-4 ]
  • [ 1030825-20-7 ]
  • 7
  • [ 21900-41-4 ]
  • [ 1030825-20-7 ]
  • 8
  • [ 1030825-20-7 ]
  • [ 110391-10-1 ]
  • [ 1413373-77-9 ]
YieldReaction ConditionsOperation in experiment
Synthesis of compound 45C53H49F05S M = 817.02 g.mol"1 19FNMR (CDCh, 282.5MHz): -115.2 (m, IF, Ar-F)+; 855.4 [M+K]+ ft-Butyllithium (1.4M in hexanes, 0.30mL, 0.412mmol, l . l eq) was slowly added to a cooled solution (-70°C) of 44 (149mg, 0.412mmol, l . l eq) in anhydrous THF-toluene (1:1, v/v, 4.8mL) under inert atmosphere. The resultant dark blue solution was stirred for 5 min at the same temperature before a cooled solution (-70°C) of cyclohexenone 8 was slowly added. The reaction mixture was stirred for 15 min at -70°C before being poured into water. The organic layer was then dried over sodium sulphate, filtered and concentrated to afford crude 45 (300mg, 98percent yield) as yellow oil which was used in the next step without further purification.
  • 9
  • [ 79669-49-1 ]
  • [ 1030825-20-7 ]
  • 10
  • [ 1030825-20-7 ]
  • [ 1432591-75-7 ]
  • [ 1432591-84-8 ]
YieldReaction ConditionsOperation in experiment
56% 2-(5-Bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene (1.5 g, 4.15 mmol) and magnesium powder (0.33 g, 13.7 mmol) were placed in a suitable reactor, followed by THF (9 mL) and 1,2-dibromoethane (95 muL). The mixture was heated to reflux. After the reaction was initiated, a solution of 2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene (2.5 g, 6.92 mmol) in THF (15 mL) was added dropwise. The mixture was stirred for another 2 hours under reflux, and was then cooled to ambient temperature and titrated to determine the concentration. The thus prepared 3-[[5-(4-fluorophenyl)-2-thienyl]methyl]-4-methylphenyl magnesium bromide (0.29 M in THF, 17 mL, 5.0 mmol) and AlCl3 (0.5 M in THF, 4.0 mL, 2.0 mmol) were mixed at ambient temperature to give a black solution, which was stirred at ambient temperature for 1 hour. To a solution of 1,6-anhydro-2,4-di-O-tert-butyldiphenylsilyl-beta-D-glucopyranose (0.64 g, 1.0 mmol) in PhOMe (3.0 mL) at ambient temperature was added n-BuLi (0.4 mL, 1.0 mmol, 2.5 M solution in Bu2O). After stirring for about 5 min the solution was then added into the above prepared aluminum mixture via syringe, followed by additional PhOMe (1.0 mL) to rinse the flask. The mixture was concentrated under reduced pressure (50 torr) at 60° C. (external bath temperature) to remove low-boiling point ethereal solvents, and PhOMe (6 mL) was then added. The remaining mixture was heated at 150° C. (external bath temperature) for 5 hours at which time HPLC assay analysis indicated a 68percent yield of 2,4-di-O-tert-butyldiphenylsilyl-1-C-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-beta-D-glucopyranoside. After cooling to ambient temperature, the reaction was treated with 10percent aqueous NaOH (1 mL), THF (10 mL) and diatomaceous earth at ambient temperature, then the mixture was filtered and the filter cake was washed with THF. The combined filtrates were concentrated and the crude product was purified by silica gel column chromatography (eluting with 1:20 MTBE/n-heptane) to give the product 2,4-di-O-tert-butyldiphenylsilyl-1-C-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-beta-D-glucopyranoside (0.51 g, 56percent) as a white powder. [0273] 1H NMR (400 MHz, CDCl3) delta 7.65 (d, J=7.2 Hz, 2H), 7.55 (d, J=7.2 Hz, 2H), 7.48 (dd, J=7.6, 5.6 Hz, 2H), 7.44-7.20 (m, 16H), 7.11-6.95 (m, 6H), 6.57 (d, J=3.2 Hz, 1H), 4.25 (d, J=9.6 Hz, 1H), 4.06 (s, 2H), 3.90-3.86 (m, 1H), 3.81-3.76 (m, 1H), 3.61-3.57 (m, 1H), 3.54-3.49 (m, 2H), 3.40 (dd, J=8.8, 8.8 Hz, 1H), 2.31 (s, 3H), 1.81 (dd, J=6.6, 6.6 Hz, 1H, OH), 1.19 (d, J=4.4 Hz, 1H, OH), 1.00 (s, 9H), 0.64 (s, 9H); 13C NMR (100 MHz, CDCl3) delta 162.1 (d, J=246 Hz, C), 143.1 (C), 141.4 (C), 137.9 (C), 136.8 (C), 136.5 (C), 136.4 (CH×2), 136.1 (CH×2), 135.25 (C), 135.20 (CH×2), 135.0 (CH×2), 134.8 (C), 132.8 (C), 132.3 (C), 130.9 (d, J=3.5 Hz, C), 130.5 (CH), 130.0 (CH), 129.7 (CH), 129.5 (CH), 129.4 (CH), 129.2 (CH), 127.6 (CH×4), 127.5 (CH×2), 127.2 (CH×2), 127.1 (d, J=8.2 Hz, CH×2), 127.06 (CH), 126.0 (CH), 122.7 (CH), 115.7 (d, J=21.8 Hz, CH×2), 82.7 (CH), 80.5 (CH), 79.4 (CH), 76.3 (CH), 72.9 (CH), 62.8 (CH2), 34.1 (CH2), 27.2 (CH3×3), 26.7 (CH3×3), 19.6, (C), 19.3 (CH3), 19.2 (C); LCMS (ESI) m/z 938 (100, [M+NH4]+), 943 (10, [M+Na]+). 2
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; ;