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[ CAS No. 3133-81-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3133-81-1
Chemical Structure| 3133-81-1
Chemical Structure| 3133-81-1
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Quality Control of [ 3133-81-1 ]

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Product Details of [ 3133-81-1 ]

CAS No. :3133-81-1 MDL No. :MFCD02683110
Formula : C11H10O2S Boiling Point : -
Linear Structure Formula :- InChI Key :FDBXIMKCWBPTDG-UHFFFAOYSA-N
M.W : 206.26 Pubchem ID :268658
Synonyms :

Calculated chemistry of [ 3133-81-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.18
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.07
TPSA : 54.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.62
Log Po/w (XLOGP3) : 3.49
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 2.55
Log Po/w (SILICOS-IT) : 3.95
Consensus Log Po/w : 3.12

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.66
Solubility : 0.045 mg/ml ; 0.000218 mol/l
Class : Soluble
Log S (Ali) : -4.32
Solubility : 0.00992 mg/ml ; 0.0000481 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.81
Solubility : 0.0318 mg/ml ; 0.000154 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 3133-81-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3133-81-1 ]

* 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 [ 3133-81-1 ]

[ 3133-81-1 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 3133-81-1 ]
  • [ 3133-88-8 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.25h; Inert atmosphere; Cooling with ice; Stage #2: With water; ammonium chloride In tetrahydrofuran Cooling with ice; 1.2 (2) 3-Methylbenzothiophene-2-methanol To an ice-cold suspension of lithium aluminum hydride (103 mg, 2.72 mmol) in THF (4.4 mL) was added dropwise over 15 minutes under N2 atmosphere, a solution of the above- mentioned methyl 3-methylbenzothiophene-2-carboxylate (560 mg, 2.72 mmol) in THF (1 mL). The mixture was stirred under ice-cooling for 45 minutes, then at room temperature for 5 minutes, to which was added dropwise under ice-cooling saturated aqueous ammonium chloride solution. The mixture was filtered through a layer of Celite, washed with ethyl acetate. Combined organic layers were washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give the titled compound as a white crystal (483 mg, yield 99%). 1H NMR (CDCl3, 400MHz): δ= 1.79(1H,t,J=6Hz), 2.39(3H,s), 4.91(2H,d,J=6Hz), 7.3-7.4(2H,m), 7.67(1H,dd,J=1Hz,8Hz), 7.81(1H,dd,J=1Hz,8Hz).
83% Stage #1: 3-methylbenzo[b]thiophene-2-carboxylic acid methyl ester With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Stage #2: With Glauber's salt In tetrahydrofuran; water at 0 - 20℃; for 2.5h; 7 Add a solution of methyl 3-methylbenzo(Z?)thiophen-2-carboxylate (5.00 g, 24.2 mmol) in THF (25 mL) dropwise to a IM solution of lithium aluminum hydride in THF (121 mL, 121 mmol) at 0°C. Stir 1 hour. Add an excess of sodium sulfate decahydrate portionwise (slowly at first), stir for 30 minutes at O0C, then 2 hours at room temperature. Filter, and wash the cake with THF. Concentrate the combined filtrates to afford the drawn product as a white solid (3.60 g, 83%): 1H NMR (CDCl3) δ 7.81 (m, IH), 7.68 (m, IH), 7.35 (m, 2H), 4.92 (d, 2H), 2.40 (s, 3H), 1.77 (t, IH).
With lithium aluminium tetrahydride; diethyl ether
  • 2
  • [ 72666-86-5 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
66% In methanol; benzene for 8h; Irradiation;
  • 3
  • [ 28195-16-6 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
66% In methanol; benzene Irradiation;
YieldReaction ConditionsOperation in experiment
aus 2-Carboxy-3-methyl-benzo<b>thiophen in abs. Me. <konz. H2SO4> (Siedetemp., 20 Std.);
Nitrierung v. 3-Methylbenzthiophen-carbonsaeure (+CH2N2 ?);
11c, AlCl3, HCl, CH3OH;
Sulfenylchlorid 9, 1) AlCl3, 2) MeOH;

  • 5
  • [ 67-56-1 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 6
  • [ 4755-81-1 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 94 percent / Et3N / CH2Cl2 / 0 deg C then up to room temp. 2: 66 percent / benzene; methanol / 8 h / Irradiation
Multi-step reaction with 2 steps 1: triethylamine 2: 66 percent / benzene; methanol / Irradiation
  • 7
  • [ 108-98-5 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 94 percent / Et3N / CH2Cl2 / 0 deg C then up to room temp. 2: 66 percent / benzene; methanol / 8 h / Irradiation
Multi-step reaction with 2 steps 1: triethylamine 2: 66 percent / benzene; methanol / Irradiation
  • 8
  • [ 450-95-3 ]
  • [ 2365-48-2 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
36% Stage #1: Methyl thioglycolate With sodium hydride In tetrahydrofuran; dimethyl sulfoxide at 20℃; Inert atmosphere; Stage #2: 2-fluoroacetophenone In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 1h; 1.1 (1) Methyl 3-methylbenzothiophene-2-carboxylate To a suspension of 55% sodium hydride (390 mg, 9.69 mmol) in THF (7 mL)-DMSO (20 mL) was added methyl thioglycolate (0.64 ml) under N2 atmosphere. After ceasing of bubbling, the mixture was stirred for 15 minutes at room temperature, to which was added slowly a solution of 2-fluoroacetophenone (0.89 mL, 6.46 mmol) in DMSO(5 mL). The mixture was stirred at room temperature for 1 hour, diluted with water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to give the titled compound as a white crystal (533 mg, 36%). 1H NMR (CDCl3, 400MHz): δ= 2.78(3H,s), 3.93(3H,s), 7.4-7.5(2H,m), 7.8-7.9(2H,m).
  • 9
  • [ 3133-81-1 ]
  • 3-bromomethyl-benzo[b]thiophene-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.2% With N-Bromosuccinimide; Perbenzoic acid In dichloromethane for 3h; Reflux; (b) 3-Bromomethyl-benzo[b]thiophene-2-carboxylic acid methyl ester General procedure: To a solution of 3-methyl-benzo[b]thiophene-2-carboxylic acid methyl ester (0.200 g, 0.969 mmol) in dichloromethane, NBS (0.173 g, 0.972 mmol) and a catalytic amount of benzoylperoxide were added. The reaction mixture was refluxed for 3 hours, concentrated in vacuo, and then purified with silica gel column chromatography to obtain the target compound (0.23 g, 83.2% yield).
82% With N-Bromosuccinimide In benzene for 2h; Inert atmosphere; Reflux; 103.103a A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and reflux condenser was purged with nitrogen and charged with methyl 3- methylbenzo[^]thiophene-2-carboxylate (2.00 g, 9.70 mmol) and benzene (20 mL). N- bromosuccinimide (1.72 g, 9.70 mmol) and 2,2'-azobisisobutyronitrile (160 mg, 1.00 mmol) were added, and the mixture was refluxed for 2 h. After this time, the mixture was cooled to room temperature and filtered. The filter cake was rinsed with carbon tetrachloride (20 mL) and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford 103a in 82% yield (2.27 g) as a white solid: mp 101- 102 °C; ]H NMR (500 MHz, CDC13) δ 7.97 (m, 1H), 7.86 (m, 1H), 7.51 (m, 2H), 5.22 (s, 2H), 3.97 (s, 3H).
54% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 85℃; 12.1 Step 1 A mixture of methyl 3-methylbenzo[/>]thiophene-2-carboxyl ate (2.26 g, 11.1 mmol), N-bromosuccinimide (1.96 g, 11.10 mmol) and 2,2'-azobisisobutyronitrile (903 mg, 5.5 mmol) in benzene (30 mL) was stirred at 85 °C overnight. The mixture was concentrated under reduced pressure and purified by chromatography on silica gel (2% - 25% EtOAc in PE) to give compound 12A (1.68 g, 54% yield) as a white solid: ESI m/z 285.4, 287.4 [M+H] +.
54% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In benzene at 85℃; 15.1 [0223] Step 1: A mixture of methyl 3-methylbenzo[6]thiophene-2-carboxylate (2.26 g, 11.1 mmol), N- bromosuccinimide (1.96 g, 11.10 mmol) and 2,2'-azobisisobutyronitrile (903 mg, 5.5 mmol) in benzene (30 mL) was stirred at 85 °C overnight. The mixture was concentrated under reduced pressure and purified by chromatography on silica gel (2% - 25% EtOAc in PE) to give compound 12A (1.68 g, 54% yield) as a white solid: ESI m/z 285.4, 287.4 [M+H] +.
With N-Bromosuccinimide In benzene for 3h; Reflux; 1.b b) 3-Bromomethyl-benzo[b]thiophene-2-carboxylic acid methyl ester 3-Methyl-benzo[b]thiophene-2-carboxylic acid methyl ester (0.200 g, 0.969 mmol) was dissolved in benzene, and NBS (0.173 g, 0.972 mmol) and a catalytic amount of benzoylperoxide was added, refluxed for 3 hours, cooled to room temperature, evaporated under a reduced pressure to remove solvents, and then purified with column chromatography to obtain a target compound 3-bromomethyl-benzo[b]thiophene-2-carboxylic acid methyl ester (0.248 g, 0.870 mmol).

  • 10
  • [ 67-56-1 ]
  • [ 3133-78-6 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride for 4h; Reflux; 1.a a) 3-Methyl-benzo[b]thiophene-2-carboxylic acid methyl ester Thionyl chloride (15 g, 26 mmol) was added to methanol (100 ml), and 3-methyl-benzo[b]thiophene-2-carboxylic acid (5 g, 26.0 mmol) was dissolved, refluxed for 4 hours, and then evaporated to obtain a target compound 3-methyl-benzo[b]thiophene-2-carboxylic acid methyl ester (5.10 g, 24.7 mmol).
  • 11
  • [ 3133-81-1 ]
  • [ 1346672-45-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux 2.1: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere 3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 14 h / 20 °C 3.2: pH 5
  • 12
  • [ 3133-81-1 ]
  • C18H16BrNO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux 2: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere
  • 13
  • [ 3133-81-1 ]
  • [ 1346672-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux 2.1: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere 3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 14 h / 20 °C 3.2: pH 5 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere
  • 14
  • [ 3133-81-1 ]
  • [ 1346672-48-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux 2.1: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere 3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 14 h / 20 °C 3.2: pH 5 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere 5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux
  • 15
  • [ 3133-81-1 ]
  • [ 1346669-52-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / benzene / 2 h / Inert atmosphere; Reflux 2.1: caesium carbonate / acetonitrile / 14 h / 50 °C / Inert atmosphere 3.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 14 h / 20 °C 3.2: pH 5 4.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 14 h / 20 °C / Inert atmosphere 5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux 6.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; 1,4-dioxane; water / 14 h / Inert atmosphere; Reflux
  • 16
  • [ 3133-81-1 ]
  • [ 1133435-54-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h
  • 17
  • [ 3133-81-1 ]
  • C12H5Cl2NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4: thionyl chloride / dichloromethane / 4 h / 20 °C 5: Perbenzoic acid; N-chloro-succinimide / dichloromethane / 12 h / Reflux 6: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 5 h / 40 °C 7: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C
  • 18
  • [ 3133-81-1 ]
  • [ 1133435-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
  • 19
  • [ 3133-81-1 ]
  • [ 1133435-56-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4: thionyl chloride / dichloromethane / 4 h / 20 °C
  • 20
  • [ 3133-81-1 ]
  • [ 1133435-57-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4: thionyl chloride / dichloromethane / 4 h / 20 °C 5: Perbenzoic acid; N-chloro-succinimide / dichloromethane / 12 h / Reflux
  • 21
  • [ 3133-81-1 ]
  • [ 1470023-21-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4: thionyl chloride / dichloromethane / 4 h / 20 °C 5: Perbenzoic acid; N-chloro-succinimide / dichloromethane / 12 h / Reflux 6: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 5 h / 40 °C
  • 22
  • [ 3133-81-1 ]
  • [ 1470023-22-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4: thionyl chloride / dichloromethane / 4 h / 20 °C 5: Perbenzoic acid; N-chloro-succinimide / dichloromethane / 12 h / Reflux 6: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 5 h / 40 °C 7: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 8: triethylamine / dichloromethane / 2 h / 0 °C
  • 23
  • [ 3133-81-1 ]
  • [ 1133435-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: N-Bromosuccinimide; Perbenzoic acid / dichloromethane / 3 h / Reflux 2: potassium carbonate / dichloromethane / 12 h 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 4: thionyl chloride / dichloromethane / 4 h / 20 °C 5: Perbenzoic acid; N-chloro-succinimide / dichloromethane / 12 h / Reflux 6: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 5 h / 40 °C 7: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C 8: triethylamine / dichloromethane / 2 h / 0 °C 9: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 5 h / 20 °C
  • 24
  • thioglycolic acid methyl ester [ No CAS ]
  • [ 445-27-2 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
50.2% With sodium hydride In tetrahydrofuran at 40℃; for 3h; (a); 3-Methyl-benzo[b]thiophene-2-carboxylic acid methyl ester General procedure: To a solution of 1-(2-fluoro-phenyl)-ethanone (886 mg, 6.41 mmol) in THF (50 ml), methyl thioglycolate (748 mg, 7.05 mmol) and 60% sodium hydride (513 mg, 12.8 mmol) were added. The reaction mixture was stirred at 40°C for 3 hours, quenched with 5% HCl solution to pH 7 and then extracted with EtOAc. The organic layer was washed with brine, dried with anhydrous sodium sulfate, and then concentrated in vacuo. The target compound was obtained by recrystallization with EtOAc/n-hexane (661 mg, 50.2% yield).50.2
  • 25
  • [ 445-27-2 ]
  • [ 2365-48-2 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
1.36 g With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 0 - 20℃; for 18h; Inert atmosphere;
  • 26
  • [ 3133-81-1 ]
  • [ 3133-78-6 ]
YieldReaction ConditionsOperation in experiment
0.742 g With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 4h;
450 mg With lithium hydroxide monohydrate In methanol; water at 75℃; for 2h; 14 A mixture of 500 mg of methyl 3-methylbenzo[b]thiophene-2-carboxylate, 121 mg of lithium hydroxide monohydrate,4 ml of water, and 12 ml of methanol was stirred for 2 hours at 75°C. After being cooled to room temperature,the reaction mixture was concentrated under reduced pressure. Water was added to the residues, and the residue waswashed three times with tert-butyl methyl ether. Concentrated hydrochloric acid was added to the aqueous layer, andthen extraction was performed three times by using tert-butyl methyl ether. The collected organic layer was washed withsaturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure, thereby obtaining 450mg of 3-methylbenzo[b]thiophene-2-carboxylic acid (hereinafter, described as a "compound 24 of the present invention").1H-NMR (CDCl3) δ: 7.88 (m, 2H), 7.49 (m, 2H), 2.82 (s, 3H).
  • 27
  • [ 3133-81-1 ]
  • [ 1415968-18-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: water; lithium hydroxide / tetrahydrofuran; methanol / 4 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -10 °C / Inert atmosphere 2.2: 16 h / -10 - 20 °C / Inert atmosphere
  • 28
  • [ 1455-18-1 ]
  • [ 124-38-9 ]
  • [ 74-88-4 ]
  • [ 3133-81-1 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 3-methylbenzothiophene; carbon dioxide With 18-crown-6 ether; cesium fluoride; lithium tert-butoxide at 160℃; for 15h; Inert atmosphere; Sealed tube; Stage #2: methyl iodide at 60℃; for 2h;
  • 29
  • [ 3133-81-1 ]
  • (2,2’-bipyridine)Zn(CF3)2 [ No CAS ]
  • methyl 3-(2,2,2-trifluoroethyl)benzo[b]thiophene-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With zinc diacetate; copper(l) cyanide; zinc trifluoromethanesulfonate; N-fluorobis(benzenesulfon)imide at 20℃; for 24h; Sealed tube; Inert atmosphere; Method C. Typical Procedure: General procedure: To a dried sealed tube (10 mL) equipped with a Teflonseptum and magnetic stir bar were added successively 4-phenylbutyl acetate (3k, 39 mg,0.20 mmol), CuCN (1.8 mg, 0.02 mmol), NFSI (189 mg, 0.60 mmol), (bpy)Zn(CF3)2(144 mg, 0.40 mmol), Zn(OTf)2 (36 mg, 0.1 mmol) and Zn(OAc)2 (18 mg, 0.1 mmol).PhCF3 (4.0 mL) were then added into the tube under nitrogen atmosphere. The resultingmixture was stirred at room temperature for 24 h. After the removal of solvent, theresidue was purified by column chromatography on silica gel with a gradient eluent ofpetroleum ether and ethyl acetate to provide the pure product5,5,5-trifluoro-4-phenylpentyl acetate (4k) as a colorless oil. Yield: 40 mg (76%).
  • 30
  • [ 3133-81-1 ]
  • C10H7NOS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 85 °C 2: ammonia / methanol / 50 °C / Sealed tube
Multi-step reaction with 2 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 85 °C 2: ammonia / methanol / 50 °C / Sealed tube
  • 31
  • [ 3133-81-1 ]
  • 2-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)-1,2-dihydro-3H-benzo[4,5]thieno[2,3-c]pyrrol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 85 °C 2: ammonia / methanol / 50 °C / Sealed tube 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / benzene / 85 °C 2: ammonia / methanol / 50 °C / Sealed tube 3: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 95 °C / Inert atmosphere
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