Home Cart 0 Sign in  

[ CAS No. 1268375-33-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1268375-33-2
Chemical Structure| 1268375-33-2
Structure of 1268375-33-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 1268375-33-2 ]

Related Doc. of [ 1268375-33-2 ]

Alternatived Products of [ 1268375-33-2 ]

Product Details of [ 1268375-33-2 ]

CAS No. :1268375-33-2 MDL No. :
Formula : C12H10Cl2O4S2 Boiling Point : -
Linear Structure Formula :- InChI Key :FWYGRZLAGNRAIJ-UHFFFAOYSA-N
M.W : 353.24 Pubchem ID :102484830
Synonyms :

Calculated chemistry of [ 1268375-33-2 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 8
Fraction Csp3 : 0.33
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 81.9
TPSA : 109.08 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.48
Log Po/w (XLOGP3) : 5.07
Log Po/w (WLOGP) : 4.62
Log Po/w (MLOGP) : 3.21
Log Po/w (SILICOS-IT) : 6.11
Consensus Log Po/w : 4.5

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.12
Solubility : 0.00265 mg/ml ; 0.00000751 mol/l
Class : Moderately soluble
Log S (Ali) : -7.1
Solubility : 0.0000279 mg/ml ; 0.0000000789 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.76
Solubility : 0.00607 mg/ml ; 0.0000172 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.21

Safety of [ 1268375-33-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1268375-33-2 ]

* 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 [ 1268375-33-2 ]

[ 1268375-33-2 ] Synthesis Path-Downstream   1~37

  • 1
  • [ 251-41-2 ]
  • [ 1268375-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere 2.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / 25 °C / Inert atmosphere 2.2: 1 h / -40 - 20 °C / Inert atmosphere 3.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / -20 °C / Inert atmosphere 3.2: 12 h / -20 - 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: N-chloro-succinimide / N,N-dimethyl-formamide / 25 °C 2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 20 °C / Inert atmosphere 2.2: -80 - 0 °C 3.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / -20 °C
  • 2
  • [ 1268375-16-1 ]
  • [ 623-49-4 ]
  • [ 1268375-33-2 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: ethyl 2,5-dichlorothieno[3,2-b]thiophene-3-carboxylate With 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride In tetrahydrofuran at -20℃; Inert atmosphere; Stage #2: ethyl cyanoformate In tetrahydrofuran at -20 - 20℃; for 12h; Inert atmosphere; regioselective reaction;
With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at -20℃; 1.2 Take a two-necked round bottom flask, treat it with anhydrous and anaerobic solution, add tetramethylpiperidine MgCl.LiCl catalyst to a tetrachlorofuran solution of dichlorothiophene under nitrogen protection, and stir the reaction at room temperature for 1 to 5 hours To reduce the reaction temperature, it can be between -80 and 0 ° C. Ethyl cyanoformate is added.Perform unilateral aldolization and TLC monitoring to obtain unilateral aldolization product 2; repeat the above aldolization. After the reaction is completed, add an aqueous ammonium chloride solution to the reaction solution to quench it, and transfer the reaction liquid to the The liquid funnel was extracted with diethyl ether, and the organic phase was dried over anhydrous sodium sulfate. After spin-drying, it was passed through the column with petroleum ether / dichloromethane eluent to obtain a white solid, which is a bilateral aldolization product 3. Among them, compound 1, tetramethyl The ratio of the piperidine MgCl.LiCl, ethyl cyanoformate, and tetrahydrofuran is 10-18 mmol: 10-30 mmol: 5-25 mmol: 30-70 mL; the yield is 74.5%
  • 3
  • [ 1268375-33-2 ]
  • [ 1268375-37-6 ]
YieldReaction ConditionsOperation in experiment
81% With palladium 10% on activated carbon; ammonium formate In ethanol; water at 120℃; for 4h; Inert atmosphere; Microwave irradiation;
  • 4
  • [ 1268375-33-2 ]
  • [ 1268375-67-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; ammonium formate / ethanol; water / 4 h / 120 °C / Inert atmosphere; Microwave irradiation 2.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / -40 °C / Inert atmosphere 2.2: 0.25 h / Inert atmosphere 2.3: 1 h / -40 °C / Inert atmosphere
  • 5
  • [ 1268375-33-2 ]
  • [ 1268375-68-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; ammonium formate / ethanol; water / 4 h / 120 °C / Inert atmosphere; Microwave irradiation 2.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / -40 °C / Inert atmosphere 2.2: 0.25 h / Inert atmosphere 2.3: 1 h / -40 °C / Inert atmosphere
  • 6
  • [ 39076-88-5 ]
  • [ 1268375-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / 25 °C / Inert atmosphere 1.2: 1 h / -40 - 20 °C / Inert atmosphere 2.1: 2,2,6,6-tetramethylpiperidinyl magnesium chloride-lithium chloride / tetrahydrofuran / -20 °C / Inert atmosphere 2.2: 12 h / -20 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / 20 °C / Inert atmosphere 1.2: -80 - 0 °C 2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran / -20 °C
  • 7
  • [ 1268375-33-2 ]
  • C40H78SSn [ No CAS ]
  • C68H112O4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide; toluene at 120℃; for 24h; Inert atmosphere;
  • 8
  • [ 1268375-33-2 ]
  • C54H68N4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 4: aluminum (III) chloride / dichloromethane / 0 - 20 °C 5: titanium tetrachloride; pyridine / chlorobenzene / 0 - 20 °C / Inert atmosphere
  • 9
  • [ 1268375-33-2 ]
  • C48H70Cl2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C
  • 10
  • [ 1268375-33-2 ]
  • C64H102Cl2O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C
  • 11
  • [ 1268375-33-2 ]
  • C70H100N4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 4: aluminum (III) chloride / dichloromethane / 0 - 20 °C 5: titanium tetrachloride; pyridine / chlorobenzene / 0 - 20 °C / Inert atmosphere
  • 12
  • [ 1268375-33-2 ]
  • C48H68O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 4: aluminum (III) chloride / dichloromethane / 0 - 20 °C
  • 13
  • [ 1268375-33-2 ]
  • C64H100O2S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux 3: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 4: aluminum (III) chloride / dichloromethane / 0 - 20 °C
  • 14
  • [ 1268375-33-2 ]
  • C48H72O4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux
  • 15
  • [ 1268375-33-2 ]
  • C64H104O4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide; toluene / 24 h / 120 °C / Inert atmosphere 2: sodium hydroxide / methanol; tetrahydrofuran / Reflux
  • 16
  • [ 1268375-33-2 ]
  • C32H62SSn [ No CAS ]
  • C52H80O4S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide; toluene at 120℃; for 24h; Inert atmosphere;
  • 17
  • [ 1193633-94-1 ]
  • [ 1268375-33-2 ]
  • 5,5"-bis-triisopropylsilanyl-[2,2';5',2"]ter[thieno[3,2-b]thiophene]-3',6'-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: triisopropyl-thieno[3,2-b]thiophen-2-yl-silane With n-butyllithium In tetrahydrofuran; hexane at -78 - -30℃; for 2.5h; Stage #2: With tributyltin chloride In tetrahydrofuran; hexane at -78 - 23℃; for 17h; Stage #3: 2,5-dichloro-thieno[3,2-b]thiophene-3,6-dicarboxylic acid diethyl ester With tetrakis(triphenylphosphine) palladium(0) In toluene at 70℃; for 65h; 1.a a) Synthesis of 5,5″-Bis-triisopropylsilanyl-[2,2′;5′,2″]ter[thieno[3,2-b]thio-phene]-3′,6′-dicarboxylic acid diethyl ester (3) (0233) To a solution of triisopropyl-thieno[3,2-b]thiophen-2-yl-silane 1 (2.4 g, 8.0 mmol) in anhydrous tetrahydrofuran (60 cm3) at -78° C. was added dropwise n-butyllithium (4.2 cm3, 10 mmol, 2.5 M in hexane) over 20 minutes. The mixture was stirred at -78° C. for 1 hour and at -30° C. for 1.5 hours before cooling back to -78° C. Tributyltin chloride (3.2 cm3, 11 mmol) was added all at once and the reaction mixture allowed to warm to 23° C. over 17 hours. The solvent was removed in vacuo and the residue taken up in anhydrous toluene (50 cm3). 2,5-Dichloro-thieno[3,2-b]thiophene-3,6-dicarboxylic acid diethyl ester 2 (1.13 g, 3.2 mmol) and tetrakis(triphenyl-phosphine)palladium(0) (0.5 g, 0.4 mmol) were added and the reaction mixture stirred at 70° C. for 65 hours. The solvent was removed in vacuo and the residue triturated in methanol (250 cm3). The solid was collected by filtration and washed with methanol (2×200 cm3) and water (200 cm3). The solid was further purified by silica plug (dichloromethane) and the residue triturated in acetone (200 cm3). The solid was then collected by filtration to give 5,5″-bis-triisopropylsilanyl-[2,2′;5′,2″]ter[thieno[3,2-b]thiophene]-3′,6′-dicarboxylic acid diethyl ester 3 (2.20 g, 78%) as a yellow solid. (0234) 1H-NMR (300 MHz, CDCl3) 1.11-1.18 (36H, m), 1.31-1.48 (12H, m), 4.43 (4H, q, J 7.2), 7.37 (2H, s), 7.82 (2H, s)
  • 18
  • [ 1268375-33-2 ]
  • C44H54BNO4 [ No CAS ]
  • [ 709022-63-9 ]
  • C64H61NO6S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium dihydrogenphosphate; palladium diacetate In 1,4-dioxane; vaseline Inert atmosphere; Reflux; 3 Synthesis of Compounds of Structure (IX-2): In a three-necked round bottom flask, 4 g of the compound of the formula (VI-1), 2.26 g of the compound of the formula (VII-1), 2.10 g of intermediate (VIII-2) was dissolved in 60 mL of a dioxane / water mixed solvent(Volume ratio: 5/1), 68 mg of palladium acetate was added under argon atmosphere,123 mg of the organophosphine ligand 2-dicyclohexylphosphino-2 ', 6'-dimethoxybiphenyl (Sphos) and 6.32 g of potassium phosphate,And the reaction was carried out under reflux in an argon atmosphere overnight. After completion of the reaction, the reaction system was cooled to room temperature, and 30 mL of the reaction mixture was addedWater, and the mixture was extracted three times with chloroform. The organic phases were combined and the organic phase was dried over anhydrous sodium sulfate, filteredThe desiccant was removed and the filtrate was concentrated and washed with toluene (boiling range 60-90 ° C) / petroleum ether (2/1 by volume)To afford 3.47 g of the compound of structure (IX-2) in 58% yield.
  • 19
  • [ 1268375-33-2 ]
  • [ 709022-63-9 ]
  • diethyl 2,5-di(anthracen-9-yl)thieno[3,2-b]thiophene-3,6-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 110℃; for 15h; Inert atmosphere;
  • 20
  • [ 1268375-33-2 ]
  • C29H52SSiSn [ No CAS ]
  • C46H60O4S4Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.01 g With tris-(dibenzylideneacetone)dipalladium(0); XPhos In N,N-dimethyl-formamide; toluene at 80℃; for 20h; 104 Intermediate 47 To a degassed solution of intermediate 9 (1 .80 g, 5.10 mmol) and intermediate 46 (7.8 g, 12 mmol, 90% purity) in anhydrous toluene (60 cm3) and anhydrous Λ/,/V-dimethylformamide (10 cm3) is added 2- dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (850 mg, 1 .78 mmol) and tris(dibenzylideneacetone)dipalladiunn(0) (187 mg, 0.20 mmol) and the mixture stirred at 80 °C for 20 hours. The reaction mixture is allowed to cool to 23 °C and the solvents removed in vacuo. The residue is triturated in ice-cooled diethyl ether (50 cm3), filtered off and the solid washed with 40-60 petrol (2 x 20 cm3) to give intermediate 47 (3.01 g, 68%) as a yellow solid. 1H NMR (400 MHz, CDCIs) 8.15 (2H, d, J 1 .6), 7.90 (2H, d, J 8.2), 7.62 (2H, dd, J 8.2, 1 .6), 7.57 (2H, s), 4.34 (4H, q, J 7.1 ), 1 .40 - 1 .49 (6H, m), 1 .32 (6H, t, J 7.1 ), 1 .19 (36H, d, J 7.5).
  • 21
  • [ 39076-88-5 ]
  • [ 541-41-3 ]
  • [ 1268375-33-2 ]
YieldReaction ConditionsOperation in experiment
91% With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 5 - 23℃; for 43h; 81 Intermediate 9 To a solution of 2,5-dichloro-thieno[3,2-b]thiophene (17.3 g, 82.7 mmol) in anhydrous tetrahydrofuran (173 cm3) at 5 °C is added ethyl chloroformate (23.7 cm3, 248 mmol). A solution of 2,2,6,6- tetramethylpiperidinylmagnesium chloride lithium chloride complex (207 cm3; 207 mmol, 1 .0 M in tetrahydrofuran) is then added dropwise over 1 hour. The reaction is slowly warmed to 23 °C and stirred for 42 hours. Water (200 cm3) is added, the mixture stirred for 10 minutes and the solid collected by filtration and washed with water (2 x 100 cm3). The solid is triturated in acetone (200 cm3), the solid collected by filtration and washed with acetone (2 x 100 cm3) to give intermediate (26.6 g, 91 %) as a white solid. 1H N MR (400 MHz, CDCIs) 4.46 (4H, q, J 7.1 ), 1 .47 (6H, t, J 7.1 ).
91% With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 0 - 23℃; for 43h; 1 Intermediate 1 To a solution of 2,5-dichloro-thieno[3,2-b]thiophene (17.3 g, 82.7 mmol) in anhydrous tetrahydrofuran (173 cm3) at 5° C. is added ethyl chloroformate (23.7 cm3, 248 mmol). A solution of 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex (207 cm3, 207 mmol, 1.0 M in tetrahydrofuran) is then added dropwise over 1 hour. The reaction is slowly warmed to 23° C. and stirred for 42 hours. Water (200 cm3) is added, the mixture stirred for 10 minutes and the solid collected by filtration and washed with water (2×100 cm3). The solid is triturated in acetone (200 cm3), collected by filtration and washed with acetone (2×100 cm3) to give intermediate 1 (26.6 g, 91%) as a white solid. 1H NMR (400 MHz, CDCl3) 4.46 (4H, q, J 7.1), 1.47 (6H, t, J 7.1).
  • 22
  • [ 1268375-33-2 ]
  • C66H84O6S4Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 100 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1.08 h / -78 °C 2.2: 65 h / -78 °C
  • 23
  • [ 1268375-33-2 ]
  • C62H64O6S4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / 100 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1.08 h / -78 °C 2.2: 65 h / -78 °C 3.1: amberlyst 15 strong acid / toluene / 17.17 h / 75 °C 3.2: 17 h / 0 - 65 °C
  • 24
  • [ 1268375-33-2 ]
  • [ 128055-72-1 ]
  • C19H21ClO4S3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With tetrakis(triphenylphosphine) palladium(0) In toluene at 85℃; for 17h; Inert atmosphere; 108 Intermediate 52 A mixture of intermediate 9 (7.1 g, 20 mmol), trimethyl-(5-tributylstannanyl- thiophen-2-yl)-silane (10 g, 23 mmol) and anhydrous toluene (300 cm3) is degassed by nitrogen for 25 minutes. To the mixture is added tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) and the mixture further degassed for 15 minutes. The mixture is stirred at 85 °C for 17 hours. The reaction mixture is filtered hot through a celite plug and washed through with hot toluene. The crude product is purified using silica gel column chromatography (40-60 petrol :dichloromethane: 4:1 ) to give intermediate 52 (2.3 g, 21 %) as a pale yellow solid. 1H-NMR (400 MHz, CDCIs) 7.40 (1 H, d, J 3.7), 6.99 - 7.03 (1 H, m), 4.13 - 4.29 (4H, m), 1 .15 - 1 .28 (6H, m), 0.10 - 0.37 (9H, s).
21% With tetrakis(triphenylphosphine) palladium(0) In toluene at 85℃; for 17h; 7 Intermediate 12 A mixture of intermediate 1 (7.1 g, 20 mmol), trimethyl-(5-tributylstannanyl-thiophen-2-yl)-silane (10 g, 23 mmol) and anhydrous toluene (300 cm3) is degassed by nitrogen for 25 minutes. To the mixture is added tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.4 mmol) and the mixture further degassed for 15 minutes. The mixture is stirred at 85° C. for 17 hours. The reaction mixture is filtered hot through a celite plug and washed through with hot toluene. The crude is purified by column chromatography (40-60 petrol:dichloromethane: 4:1) to give intermediate 12 (2.3 g, 21%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) 7.40 (1H, d, J 3.7), 6.99-7.03 (1H, m), 4.13-4.29 (4H, m), 1.15-1.28 (6H, m), 0.10-0.37 (9H, s).
  • 25
  • [ 1268375-33-2 ]
  • [ 128055-72-1 ]
  • 2,5-bis-(5-trimethylsilanylthiophen-2-yl)thieno[3,2-b]thiophene-3,6-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 18h; 81 Intermediate 10 Trimethyl-(5-tributylstannanyl-thiophen-2-yl)-silane (30.5 g, 61 .7 mmol), intermediate 9 (10.0 g, 28.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (657 mg, 0.57 mmol) are suspended in anhydrous toluene (100 cm3) and heated at 100 °C for 18 hours. The reaction is cooled to 23 °C and methanol (250 cm3) added. The suspension is cooled in an ice-bath, the solid collected by filtration and washed with methanol (200 cm3). The crude was purified by silica pad (dichloromethane) followed by flash chromatography eluting with 40-60 petrol:dichloromethane; 60:40 to give intermediate 10 (7.68g, 46%) as a yellow solid. 1H NMR (400 MHz, CDCIs) 7.42 (2H, d, J 3.5), 7.02 (2H, d, J 3.5), 4.19 (4H, q, J 7.1 ), 1 .19 (6H, t, J 7.1 ), 0.15 (18H, s).
46% With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 18h; 1 Intermediate 2 Trimethyl-(5-tributylstannanyl-thiophen-2-yl)-silane (30.5 g, 61.7 mmol), intermediate 1 (10.0 g, 28.3 mmol) and tetrakis(triphenylphosphine) palladium(0) (657 mg, 0.57 mmol) are suspended in anhydrous toluene (100 cm3) and heated at 100° C. for 18 hours. The reaction is cooled to 23° C. and methanol (250 cm3) added. The suspension is cooled in an ice-bath, the solid collected by filtration and washed with methanol (200 cm3). The crude is purified by silica pad (dichloromethane) followed by column chromatography (40-60 petrol:dichloromethane; 60:40) to give intermediate 2 (7.68 g, 46%) as a yellow solid. 1H NMR (400 MHz, CDCl3) 7.42 (2H, d, J 3.5), 7.02 (2H, d, J 3.5), 4.19 (4H, q, J 7.1), 1.19 (6H, t, J 7.1), 0.15 (18H, s).
  • 26
  • [ 1268375-33-2 ]
  • [ 1193633-95-2 ]
  • 5,5"-bis-triisopropylsilanyl-[2,2';5',2"]ter[thieno[3,2-b]thiophene]-3',6'-dicarboxylic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0) In toluene at 85℃; for 17h; Inert atmosphere; 90 Intermediate 24 A mixture of intermediate 9 (7.5 g, 21 mmol), intermediate 23 (17.8 g, 30.4 mm) and anhydrous toluene (300 cm3) is degassed by nitrogen for 25 minutes. To the mixture is added tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.43 mmol) and the mixture further degassed for 15 minutes. The mixture is stirred at 85 °C for 17 hours. The reaction mixture is filtered hot through a celite plug (50 g) and washed through with hot toluene (100 cm3). The solvent reduced in vacuo to 100 cm3 and cooled in an ice bath to form a suspension. The product is filtered, washed with water (100 cm3) and methanol (100 cm3), collected and dried under vacuum to give intermediate 24 (9.5 g, 71 %) as a yellow crystalline solid. 1H-NMR (400 MHz, CDCIs) 7.75 (2H, d, J 0.7), 7.30 (2H, d, J 0.7), 4.36 (4H, q, J 7.2), 1 .23-1 .43 (12H, m), 1 .07 (36H, d, J 7.3).
71% With tetrakis(triphenylphosphine) palladium(0) In toluene at 85℃; for 17h; 17 Intermediate 28 A mixture of 2,5-dichloro-3,6-diethyl ester-thieno[3,2-b]thiophene-3,6-dicarboxylic acid (7.5 g, 21 mmol), tributyl[5-[tris(1-methylethyl)silyl]thieno[3,2-b]thien-2-yl]-stanne (17.8 g, 30.4 mm) and anhydrous toluene (300 cm3) is degassed for 25 minutes. To the mixture is added tetrakis(triphenylphosphine)palladium(0) (500 mg, 0.43 mmol) and the mixture further degassed for 15 minutes. The mixture is stirred at 85° C. for 17 hours and then filtered hot through a celite plug (hot toluene). The solvent reduced in vacuo to 100 cm3 and cooled in an ice bath to form a suspension. The product is filtered, washed with water (100 cm3) and methanol (100 cm3) to give intermediate 28 (9.5 g, 71%) as a yellow crystalline solid. 1H NMR (400 MHz, CDCl3) 7.75 (2H, d, J 0.7), 7.30 (2H, d, J 0.7), 4.36 (4H, q, J 7.2), 1.23-1.43 (12H, m), 1.07 (36H, d, J 7.3).
  • 27
  • [ 1268375-33-2 ]
  • C64H72S2Se2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / Inert atmosphere; Reflux 2.1: magnesium / tetrahydrofuran-d8 / Reflux 2.2: amberlyst 15 / 5 h / 80 °C / Inert atmosphere
  • 28
  • [ 1268375-33-2 ]
  • C66H72O2S2Se2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 12 h / Inert atmosphere; Reflux 2.1: magnesium / tetrahydrofuran-d8 / Reflux 2.2: amberlyst 15 / 5 h / 80 °C / Inert atmosphere 3.1: trichlorophosphate / 1,2-dichloro-ethane / 80 °C
  • 29
  • [ 1268375-33-2 ]
  • [ 116886-71-6 ]
  • C20H16O4S2Se2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1 g With tetrakis(triphenylphosphine) palladium(0) In toluene for 12h; Inert atmosphere; Reflux;
  • 30
  • [ 1268375-33-2 ]
  • [ 24388-23-6 ]
  • C24H20O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.3% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In toluene at 60 - 120℃; Inert atmosphere; 1.3 (3) Synthesis of compound 4 Take a two-necked round bottom flask and treat it with anhydrous and oxygen. Add product 3, phenylboron, palladium catalyst, cesium carbonate in sequence, replace the gas 3 times, and add toluene solvent under nitrogen protection for Suzuki coupling reaction. The reaction was allowed to proceed overnight at 120 ° C. After the reaction was monitored by TLC, it was cooled to room temperature and quenched with water. The reaction solution was transferred to a separating funnel and extracted with dichloride. The organic phase was dried over anhydrous sodium sulfate and spin-dried with petroleum. The ether / dichloromethane eluent was passed through the column to obtain a pale yellow solid; wherein the compound 3, phenylboron, palladium catalyst, cesium carbonate, and toluene had a ratio of 5-20 mmol: 12-32 mmol: 1-5 mmol: 30-90 mmol: 15 40mL; yield is 83.3%;
  • 31
  • [ 1268375-33-2 ]
  • C24H16O4S6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0) In toluene Inert atmosphere; Reflux; 1.1 Under argon atmosphere, 1g (2.83mmol) (1),3.644g (8.49mmol) (2) and 164mg (0.142mmol) of Ph(PPh3)4 were added to a 100mL two-necked round bottom medium flask, and degassed with argon 3 times.Then 30 mL of anhydrous toluene was poured into the mixture, and refluxed overnight.The reaction solution was cooled to room temperature, poured into 100 mL of anhydrous methanol to precipitate and filtered,Then wash with a large amount of petroleum ether, ethyl acetate and methanol.
  • 32
  • [ 1268375-33-2 ]
  • C34H44O4S5Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0) / toluene / 17 h / 85 °C 2: tetrakis(triphenylphosphine) palladium(0) / toluene / 17 h / 85 °C
  • 33
  • [ 1268375-33-2 ]
  • [ 504441-11-6 ]
  • C24H29ClO4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 3h; Inert atmosphere; Schlenk technique;
  • 34
  • [ 1268375-33-2 ]
  • C66H72S5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tetrakis-(triphenylphosphine)-palladium / toluene / 24 h / 110 °C / Inert atmosphere 2.1: tetrakis-(triphenylphosphine)-palladium / toluene / 24 h / 110 °C / Inert atmosphere 3.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 3.3: 0.03 h / 90 °C / Inert atmosphere
  • 35
  • [ 1268375-33-2 ]
  • C68H72O2S5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tetrakis-(triphenylphosphine)-palladium / toluene / 24 h / 110 °C / Inert atmosphere 2.1: tetrakis-(triphenylphosphine)-palladium / toluene / 24 h / 110 °C / Inert atmosphere 3.1: tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C / Inert atmosphere 3.3: 0.03 h / 90 °C / Inert atmosphere 4.1: 1,2-dichloro-ethane / 13 h / 20 - 85 °C / Inert atmosphere
  • 36
  • [ 1268375-33-2 ]
  • C22H16O4S5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium / toluene / 24 h / 110 °C / Inert atmosphere 2: tetrakis-(triphenylphosphine)-palladium / toluene / 24 h / 110 °C / Inert atmosphere
  • 37
  • [ 1268375-33-2 ]
  • [ 54663-78-4 ]
  • C16H13ClO4S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis-(triphenylphosphine)-palladium In toluene at 110℃; for 24h; Inert atmosphere; (1) Add 3,6-dichloro-5,6-thieno[3,2-b]thiophenedicarboxylate diethyl ester (1), (1g), 2-tri-n-butyltinthiophene to a 100mL two-necked flask (a),(1.056 g) and tetrakistriphenylphosphine palladium (164 mg), and replaced the gas three times under argon protection,30 mL of anhydrous toluene was added. The reaction system was heated and refluxed at 110°C for 24h.The reaction progress was detected by TLC, and it was found that the raw materials disappeared and new products were produced. The reaction was stopped, the reaction solution was poured into 200 mL of anhydrous methanol, settled and filtered to obtain a yellow solid (2) with a yield of 61%.
Same Skeleton Products
Historical Records