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[ CAS No. 132819-92-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 132819-92-2
Chemical Structure| 132819-92-2
Chemical Structure| 132819-92-2
Structure of 132819-92-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 132819-92-2 ]

CAS No. :132819-92-2 MDL No. :MFCD30496705
Formula : C18H17NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :OJMOGUKIYRAILM-UHFFFAOYSA-N
M.W : 343.40 Pubchem ID :14783456
Synonyms :
MDK19922
Chemical Name :Ethyl 1-tosyl-1H-indole-2-carboxylate

Calculated chemistry of [ 132819-92-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.17
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 92.06
TPSA : 73.75 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) : -5.45 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.98
Log Po/w (XLOGP3) : 4.15
Log Po/w (WLOGP) : 4.44
Log Po/w (MLOGP) : 3.58
Log Po/w (SILICOS-IT) : 2.65
Consensus Log Po/w : 3.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.72
Solubility : 0.0066 mg/ml ; 0.0000192 mol/l
Class : Moderately soluble
Log S (Ali) : -5.41
Solubility : 0.00135 mg/ml ; 0.00000392 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.73
Solubility : 0.000634 mg/ml ; 0.00000185 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.96

Safety of [ 132819-92-2 ]

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 [ 132819-92-2 ]

* 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 [ 132819-92-2 ]

[ 132819-92-2 ] Synthesis Path-Downstream   1~60

  • 1
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  • 3
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  • [ 98-59-9 ]
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YieldReaction ConditionsOperation in experiment
74% With potassium tert-butylate; In tetrahydrofuran;Reflux; General procedure: Ethyl indole-2-carboxylate (3) (5mmol) was dissolved in THF (15mL); potassium tert-butoxide (7.5mmol) was then added and the mixture stirred for 15min at room temperature. Subsequently, the corresponding sulfonyl chloride (5.5mmol) was added to the reaction mixture which was heated overnight at reflux. Upon completion of the reaction, which was monitored by TLC, the mixture was concentrated in vacuo and the residue was dissolved in dichloromethane (80mL). The organic phase was washed with water (2×30mL), dried with anhydrous Na2SO4 then concentrated in vacuo. The residue was purified by flash silica gel column chromatography (gradient elution; starting eluent: hexane/ethyl acetate 6:1 v/v) to afford pure N-sulfonylated compounds.
61% Step 1)1-(Toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester To a stirred solution 1H-Indole-2-carboxylic acid ethyl ester (ig, 5.29 mmol) in dry THF at 0Cwas added sodium hydride in 60% oil dispersion (0.423g, 10.58 mmol) and stirred for 30 mm.To this mixture was added p-toluene sulfonyl chloride (2g, 10.58mmol) and stuffed for 12h. It was quenched with saturated ammonium chloride, extracted with ethyl acetate, dried over anhydrous sodium sulfate, evaporated under reduced pressure and the crude material was purified by column chromatography (silica gel, 5% EtOAc/Hexanes) to provide 1 -(toluene-4-sulfonyl)- 1 H-indole-2-carboxylic acid ethyl ester as white solid (1.1 g, 61%). MS calcd. for C18H17N045 [(M+H)i 344, obsd. 344.1.
In tetrahydrofuran; paraffin oil; Step 1 1-(4-Methylphenyl)sulfonyl-1H-indole-2-carboxylic acid ethyl ester To a stirred suspension of sodium hydride (3.7 g, 120 mmol, 80% in paraffin oil) in dry THF (75 mL), a solution of indol-2-carboxylic acid ethyl ester (18.9 g, 100 mmol) in dry THF (75 mL) was added in 1 hour with stirring while the inner temperature was maintained under 30 C. The reaction mixture was stirred for 30 min. and then a solution of p-toluenesulphonyl chloride (22.9 g, 120 mmol) in dry THF (75 mL) was added dropwise to the stirring reactant. After two hours stirring at room temperature and one hour at 45 C. the solvent was evaporated in vacuo and the residue partitioned between water and ethyl ether. The organic phase was dried over MgSO4 and the solvent evaporated to leave a solid which was recrystallized from diisopropyl ether (26.8 g, 78%), m.p. 92-95 C.
In tetrahydrofuran; paraffin oil; Step 1 1-(4-Methylphenyl)sulfonyl-1H-indole-2-carboxylic acid ethyl ester To a stirred suspension of sodium hydride (3.7 g, 120 mmol, 80% in paraffin oil) in dry THF (75 mL), a solution of indol-2-carboxylic acid ethyl ester (18.9 g, 100 mmol) in dry THF (75 mL) was added in 1 hour with stirring while the inner temperature was maintained under 30 C. The reaction mixture was stirred for 30 min. and then a solution of p-toluenesulphonyl chloride (22.9 g, 120 mmol) in dry THF (75 mL) was added dropwise to the stirring reactant. After two hours stirring at room temperature and one hour at 45 C. the solvent was evaporated in vacuo and the residue partitioned between water and ethyl ether. The organic phase was dried over MgSO4 and the solvent evaporated to leave a solid which was recrystallized from diisopropyl ether (26.8g, 78%), m.p. 92-95 C.
In tetrahydrofuran; paraffin oil; 1-(4-Methylphenyl)sulfonyl-1H-indol-2-carboxylic acid ethyl ester To a stirred suspension of sodium hydride (3.7 g, 120 mmol, 80% in paraffin oil) in dry THF (75 mL), a solution of indol-2-carboxylic acid ethyl ester (18.9 g, 100 mmol) in dry THF (75 mL) was added in 1 hour with stirring while the inner temperature was maintained under 30 C. The reaction mixture was stirred for 30 minutes and then a solution of p-toluenesulphonyl chloride (22.9 g, 120 mmol) in dry THF (75 mL) was added dropwise to the stirring reactant. After 2 hours stirring at room temperature and 1 hour at 45 C. the solvent was evaporated in vacuo and the residue partitioned between water and ethyl ether. The organic phase was dried over MgSO4 and the solvent evaporated to leave a solid which was recrystallized from diisopropyl ether (26.8 g, 78%), mp 92-95 C.
In tetrahydrofuran; paraffin oil; 1-(4-Methylphenyl)sulfonyl-1H-indol-2-carboxylic acid ethyl ester To a stirred suspension of sodium hydride (3.7 g, 120 mmol, 80% in paraffin oil) in dry THF (75 ml), a solution of indol-2-carboxylic acid ethyl ester (18.9 g, 100 mmol) in dry THF (75 mL) was added in 1 hour with stirring while the inner temperature was maintained under 30 C. The reaction mixture was stirred for 30 minutes and then a solution of p-toluenesulphonyl chloride (22.9 g, 120 mmol) in dry THF (75 mL) was added dropwise to the stirring reactant. After 2 hours stirring at room temperature and 1 hour at 45 C. the solvent was evaporated in vacuo and the residue partitioned between water and ethyl ether. The organic phase was dried over MgSO4 and the solvent evaporated to leave a solid which was recrystallized from diisopropyl ether (26.8 g, 78%), mp 92-95 C.
General procedure: Into a flask was added ethyl indole-2-carboxylate (1.0 g, 1.0 equiv), DMA (10 ml) was added to the flask under an inert atmosphere. NaH (0.32 g, 1.5 equiv) was added to the flask at -40. The reaction mixture was stirred for 1 h at -40. 4-methylbenzenesulfonyl chloride (2.01 g, 2.0 equiv) was added to the flask slowly. The reaction mixture was stirred overnight at rt. The reaction was diluted with water and extracted with ethyl acetate (3×100ml). The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, concentrated and purified by column chromatography (EtOAc/PE = 1/2) to give ethyl 1-tosl-1H-indole-2-carboxylate b (1.4 g, 77% yield)

  • 4
  • [ 132819-92-2 ]
  • ethyl (+)-N-( p-toluenesulfonyl)indolin-2-carboxylate [ No CAS ]
  • ethyl (-)-N-( p-toluenesulfonyl)indolin-2-carboxylate [ No CAS ]
  • 5
  • [ 132819-92-2 ]
  • ethyl (-)-N-( p-toluenesulfonyl)indolin-2-carboxylate [ No CAS ]
  • 6
  • [ 132819-92-2 ]
  • [ 100-52-7 ]
  • [ 1323764-48-2 ]
  • 7
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  • [ 106-95-6 ]
  • [ 104699-48-1 ]
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  • [ 1617530-99-0 ]
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  • [ 1617531-08-4 ]
  • 19
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  • [1-(toluene-4-sulfonyl)-indol-2-yl]-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.5 g With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃;Inert atmosphere; General procedure: Into a flask was added ethyl 1-tosl-1H-indole-2-carboxylate b (1.0 g 1.0 equiv) and THF (10 ml). LiAlH4 (0.28 g, 2.4 equiv) was added to the reaction slowly at 0 . The reaction was stirred overnight at rt. Ice water (100 mL) was added carefully to the flask to quench the reaction. The reaction was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine, dried with anhydrous Na2SO4, filtered, concentrated and purified by column chromatography (EtOAc/PE = 1/1) to give c (0.5 g, 57% yield).
  • 23
  • (Z)-3-Phenyl-2-(toluene-4-sulfonylamino)-acrylic acid ethyl ester [ No CAS ]
  • [ 132819-92-2 ]
  • 24
  • [ 132819-92-2 ]
  • (E)-3-dimethylamino-2-[1-(toluene-4-sulfonyl)-1H-indole-2-carbonyl]-acrylonitrile [ No CAS ]
  • 25
  • [ 132819-92-2 ]
  • [5-amino-1-(3-fluoro-4-phenoxy-phenyl)-1H-pyrazol-4-yl]-[1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone [ No CAS ]
  • 26
  • [ 132819-92-2 ]
  • [5-amino-1-(3-fluoro-4-phenoxy-phenyl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone [ No CAS ]
  • 27
  • [ 132819-92-2 ]
  • [ 75-05-8 ]
  • 3-oxo-3-[1-(toluene-4-sulfonyl)-1H-indol-2-yl]-propionitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With lithium diisopropyl amide; In tetrahydrofuran; at -78℃; for 0.333333h; Step 2)3-Oxo-3- [1-(toluene-4-sulfonyl)- 1H-indol-2-yl] -propionitrile To a stirred solution of <strong>[132819-92-2]1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester</strong> (8 g, 23.3 mmol) and acetonitrile (3.8 mL, 93.3 mmol) in dry THF (40 mL) at -78 C was added drop wise LDA (47.3 ml, 46.64 mmol) [prepared from addition of n-BuLi (25.6 mL, 46.64 mmol) to a solution of di-isopropyl amine (6.7 mL, 46.6 mmol) in dry THF (15 mL) at -78 C and stirred for 30 mm under argon]. It was stirred for 20 mm, quenched with ammonium chloride (10 mL),concentrated, extracted with ethyl acetate, dried over anhydrous sodium sulfate, evaporated under reduced pressure and purified by column chromatography (silica gel, 30% EtOAc/Hexanes) to provide 3-oxo-3- [1 -(toluene-4-sulfonyl)- 1 H-indol-2-yl] -propionitrile as sticky brown liquid (5.7 g, 72 %). MS calcd. for C18H14N2035 [(M+H)?i 339, obsd. 339.0.
  • 28
  • [ 132819-92-2 ]
  • 3-(4-(benzyloxy)benzylidene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 29
  • [ 132819-92-2 ]
  • 3-(4-methylbenzylidene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 30
  • [ 132819-92-2 ]
  • 3-(benzo[d][1,3]dioxol-5-ylmethylene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 31
  • [ 132819-92-2 ]
  • 3-(4-nitrobenzylidene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 32
  • [ 132819-92-2 ]
  • 3-(4-(4-(trifluoromethoxy)phenoxy)benzylidene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 33
  • [ 132819-92-2 ]
  • 3-(4-(trifluoromethoxy)benzylidene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 34
  • [ 132819-92-2 ]
  • C33H27NO2PS(1+)*Cl(1-) [ No CAS ]
  • 35
  • [ 132819-92-2 ]
  • 3-(4-chlorobenzylidene)cyclopenta[b]indole-1,2(3H,4H)-dione [ No CAS ]
  • 36
  • ethyl 3-(2-chlorophenyl)-1-tosylaziridine-2-carboxylate [ No CAS ]
  • [ 132819-92-2 ]
  • 37
  • [ 132819-92-2 ]
  • C19H17NO3S [ No CAS ]
  • 38
  • [ 132819-92-2 ]
  • C20H20N4O5S2 [ No CAS ]
  • 39
  • [ 132819-92-2 ]
  • N-((9-tosylpyrano[3,4-b]indol-4(1H,3H,9H)-ylidene)methyl)methanesulfonamide [ No CAS ]
  • 40
  • [ 132819-92-2 ]
  • 1-(4-toluenesulfonyl)-indoline-2-imminium chloride [ No CAS ]
  • 41
  • [ 132819-92-2 ]
  • 1-(4-toluenesulfonyl)-1H-indole-2-carboxamide [ No CAS ]
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  • [ 132819-92-2 ]
  • 1-(4-toluenesulfonyl)-1H-indole-2-hydrazide [ No CAS ]
  • 43
  • [ 132819-92-2 ]
  • tert-butyl (1-(4-toluenesulfonyl)-1H-indole-2-yl)carbamate [ No CAS ]
  • 44
  • [ 132819-92-2 ]
  • 1-(4-toluenesulfonyl)-1H-indole-2-carboxylic acid [ No CAS ]
  • 45
  • [ 1477-50-5 ]
  • [ 132819-92-2 ]
  • 46
  • [ 132819-92-2 ]
  • [5-amino-1-(2-chloro-5-hydroxy-phenyl)pyrazol-4-yl]-(1H-indol-2-yl)methanone [ No CAS ]
  • 47
  • [ 132819-92-2 ]
  • [5-amino-1-(2-chlorophenyl)pyrazol-4-yl]-(1H-indol-2-yl)methanone [ No CAS ]
  • 48
  • [ 132819-92-2 ]
  • [5-amino-1-(3H-benzimidazol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone [ No CAS ]
  • 49
  • [ 132819-92-2 ]
  • [5-amino-1-(2-methyl-3H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1H-indol-2-yl)-methanone [ No CAS ]
  • 50
  • [ 132819-92-2 ]
  • [5-amino-1-(2-ethyl-3H-benzimidazol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone [ No CAS ]
  • 51
  • [ 132819-92-2 ]
  • [5-amino-1-(1H-indol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone [ No CAS ]
  • 52
  • [ 132819-92-2 ]
  • [5-amino-1-(2-methyl-1H-indol-5-yl)pyrazol-4-yl]-(1H-indol-2-yl)methanone [ No CAS ]
  • 53
  • [ 132819-92-2 ]
  • 5-[5-amino-4-(1H-indole-2-carbonyl)pyrazol-1-yl]-1,3-dihydrobenzimidazol-2-one [ No CAS ]
  • 54
  • [ 132819-92-2 ]
  • (S)-[(S)-2-methylene-1-tosylindolin-3-yl](phenyl)methanol [ No CAS ]
  • 55
  • [ 132819-92-2 ]
  • (S)-(3-fluorophenyl)[(S)-2-methylene-1-tosylindolin-3-yl]methanol [ No CAS ]
  • 56
  • [ 132819-92-2 ]
  • (S)-[(S)-2-methylene-1-tosylindolin-3-yl](o-tolyl)methanol [ No CAS ]
  • C24H23NO3S [ No CAS ]
  • 57
  • [ 132819-92-2 ]
  • (R,E)-1-[(S)-2-methylene-1-tosylindolin-3-yl]-3-(o-tolyl)prop-2-en-1-ol [ No CAS ]
  • 58
  • [ 132819-92-2 ]
  • (R,E)-1-[(S)-2-methylene-1-tosylindolin-3-yl]hex-2-en-1-ol [ No CAS ]
  • C22H25NO3S [ No CAS ]
  • 59
  • [ 4755-77-5 ]
  • [ 243844-35-1 ]
  • [ 132819-92-2 ]
  • 60
  • [ 132819-92-2 ]
  • [ 3770-50-1 ]
YieldReaction ConditionsOperation in experiment
58% With sodium hydride In N,N-dimethyl acetamide at 60℃; for 2h; Inert atmosphere; General procedure for the detoyslation reaction. General procedure: To a suspension solution of NaH (0.4 mmol, 2.0 equiv) in dry DMA (1.0 mL) under N2 was added dropwise the solution of 4 or 5 (0.2 mmol, 1 equiv) in dry DMA (0.5 mL) by syringe. Then the mixture was heated at 60 °C until TLC showed the completion of the reaction. A saturated solution of NH4Cl was added to quench the reaction and extracted with EtOAc for one time. The organic layer was washed with water for three times, and the combined aqueous layers were extracted with EtOAc for one time. The combined organic layers were washed with brine and dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to give corresponding products 3 or 6.
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