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Chemical Structure| 18372-22-0 Chemical Structure| 18372-22-0
Chemical Structure| 18372-22-0

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CAS No.: 18372-22-0

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Product Details of [ 18372-22-0 ]

CAS No. :18372-22-0
Formula : C11H9NO3
M.W : 203.19
SMILES Code : O=C(OC)C(C1=CNC2=C1C=CC=C2)=O
MDL No. :MFCD00047173
InChI Key :VFIJGAWYVXDYLK-UHFFFAOYSA-N
Pubchem ID :588944

Safety of [ 18372-22-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 18372-22-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 9
Fraction Csp3 0.09
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 54.59
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

59.16 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.65
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.2
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.52
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.47
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.62

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.73
Solubility 0.377 mg/ml ; 0.00185 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.08
Solubility 0.17 mg/ml ; 0.000838 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.31
Solubility 0.0986 mg/ml ; 0.000485 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.98 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.67

Application In Synthesis of [ 18372-22-0 ]

* 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 [ 18372-22-0 ]

[ 18372-22-0 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 67-56-1 ]
  • [ 22980-09-2 ]
  • [ 18372-22-0 ]
  • 2
  • [ 18372-22-0 ]
  • [ 74-88-4 ]
  • [ 151490-40-3 ]
YieldReaction ConditionsOperation in experiment
91% To a solution of methyl 2-(1H-indol-3-yl)-2-oxoacetate (1.04 g, 5.12mmol, 1.00 equiv) in anhydrous DMF (25.0 mL, 0.205 H) was added sodiumhydride (57-63% suspension in mineral oil, 225 mg, 5.63 mmol, 1.10 equiv) at 0 C. The reaction mixture was stirred at 0 C for 30 mm before iodomethane (872 mg, 6.14 mmol, 1.20 equiv) was added. The reaction mixture was stirred overnight at room temperature. Thereaction was quenched with ice water (50.0 mL) and the aqueous layer was extracted with EtOAc (6 x 30.0 mL) . The organic extracts were combined, washed with 5% LiC1(aq) (5.00 mL), and then dried over Na2SO4. After being concentrated in vacuo, the residue was purified by flash chromatography on silica gel (EtCAc:hexanes = 1:1) to affordthe title compound as a white solid (1.01 g, 4.65 mmol, 91% yield) NMR Spectroscopy: H NHR (400 MHz, CDCl, 25 C, 6): 8.40-8.46 (m, lH), 8.29 (s, 1H), 7.31- 7.40 (m, 3H>, 3.95 (5, 3H), 3.84 (s, 3H) . NMR (100 MHz, CDC13, 25 C, 6): 177.0, 163.5, 140.6, 137.5, 127.1, 124.3, 23.7, 122.8, 112.9, 110.1, 52.8, 33.9. The 1H NMR data werein good agreement with values reported in the literature (N. Wang etal. 2011).
76.4% Add 1.0 g (4.9 mmol) of 5a and 10 mL of anhydrous DMF in a three-necked flask, cool to 0 0C, add 0.17 g (4.9 mmol) of 70% NaH, add to room temperature for 30 min and then cool to 0 (5.3 mmol) of CH3I was added dropwise and the reaction was allowed to proceed to room temperature for 1 h. After the reaction was completed, the reaction solution was poured into 100 mL of ice water and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, Washed with saturated brine (3 x 150 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure,The residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3: 1) to give 0.81 g of a white solid 6b, yield: 76.4%
33% Synthesisof2-(1-methylindole-3-yl)-2-oxoacetic acid, methyl ester The 3-indole glyoxylic acid, methyl ester (5.88 g) obtained in the step 1 was dissolved in N,N-dimethylformamide (180 mL), and thereto was added hydrogenated sodium (dispersed in oil at 60%, 1.4 g) in small portions while stirring at 0C. After stirring the reaction mixture for 1 hour, methyl iodide (1.2 mL) was added thereto, and stirred at 20C for 20 hrs. After adding ice-cooled water to the reaction fluid, the pH value was adjusted with 1 mol/L hydrochloric acid to become 5. Thus deposited crystals were filtrated, and washed with water. The crystals were dried under a reduced pressure to obtain 2-(1-methylindole-3-yl)-2-oxoacetic acid, methyl ester (1.96 g, 33%).
  • 3
  • [ 5781-53-3 ]
  • [ 120-72-9 ]
  • [ 18372-22-0 ]
  • 4
  • [ 879-37-8 ]
  • [ 18372-22-0 ]
  • [ 119139-23-0 ]
YieldReaction ConditionsOperation in experiment
80.2% A. Chemical Examples; Example 1; 3,4-Di-(1 H-indol-3-yl)pyrrole-2,5-dione (Compound 1); Potassium tert-butoxide (0.976 g, 8.7 mmol) was added to a stirred suspension of (1 H-indol-3-yl)acetamide (0.5 g, 2.8 mmol) and methyl 3-indolylglyoxylate (0.650, 3.15 mmol) in anhydrous tetrahydrofuran (15 ml), under argon at -10C. After 15 minutes the resultant dark red solution was allowed to warm to 20C over 3.5 hours. Concentrated hydrochloric acid (2ml) was added with cooling, and the orange-red precipitate then dissolved in ethyl acetate by stirring overnight. The organic phase was washed with water and brine, dried (magnesium sulphate) and evaporated to give the title compound as red crystals (0.780 g, 80.2% yield), mp 234C. 1H-NMR (DMSO-d6, No./ppm) : 11.6 (br s, 1 H), 10.95 (br s, 1 H), 7.68 (s, 1 H), 7.38 (d, 1 H), 6.98 (t, 1 H), 6.8 (d, 1 H), 6.6 (t, 1 H).
75% With potassium tert-butylate; In tetrahydrofuran; at 0 - 20℃; for 4.5h;Inert atmosphere; A three-necked flask equipped with a magnetic stirrer and two addition funnels was charged with indole (10.1 g, 0.086 mol) and 100 mL of diethyl ether. Oxalyl chloride (7.3 mL, 0.086 mol) was added dropwise to the solution at 0 C under nitrogen in 0.5 h. Yellow precipitate were formed and the reaction mixture was stirred for another 0.5 h. The reaction mixture was cooled to -70 C by dry-ice, then sodium methylate (25 % solution in methanol, 37.3 g, 0.173 mol) was added dropwise to the reaction mixture in 1 h. After that the reaction mixture was warmed to 0 C and 50 mL of water was added. The precipitate were filtered, washed with water several times, and then dried at 60 C under vacuum. The product of methyl indolyl-3- glyoxylate was obtained as a yellow powder and used without further purification. Yield 90 %. A three-necked flask equipped with a magnetic stirrer and an addition funnel was charged with 3-indoleacetamide (8.0 g, 0.046 mol), methyl indolyl-3-glyoxylate (10.0 g, 0.049 mol) and 80 mL of tetrahydrofuran. A solution of potassium tert-butoxide (15.2 g, 0.135 mol) in 130 mL of tetrahydrofuran was added dropwise to the reaction mixture at 0 C under nitrogen in 1.5 h. Then the reaction mixture was warmed to room temperature and stirred for 3 h. A solution of Hydrochloric acid (35 % in water, 64 mL) was added dropwise to the reaction mixture in 1 h. Then 200 mL of ethyl acetate and 100 mL of water were added and stirred for dissolving. The organic phase was separated, washed with water several times until neutral, and then washed with brine once, dried over anhydrous sodium sulfate. The sodium sulfate was filtered and the solution was concentrated. The product was crystallized by adding a 1:1 (v/v) mixture of ethyl acetate and n-hexane dropwise to the concentrated solution at 50~60 C. The pure product of 3,4-bisindolylmaleimide was obtained as a red crystal.
  • 5
  • [ 67-56-1 ]
  • [ 1477-49-2 ]
  • [ 18372-22-0 ]
YieldReaction ConditionsOperation in experiment
69% Synthesis of 3-indole glyoxylic acid, methyl ester Commercially available 3-indole glyoxylic acid (9.55 g) was suspended in methylene chloride (300 mL), and cooled on ice. Thereafter, to the suspension was added oxalyl chloride (8.8 mL), followed by stirring at 20C for 20 hrs. The reaction fluid was cooled on ice, and after adding methanol (190 mL) thereto, the reaction fluid was stirred at 25C for 1 hour. To the reaction fluid were added water and methylene chloride, and thus deposited crystals were filtrated, followed by washing of the crystals with methylene chloride. The crystals were dried under a reduced pressure to obtain 3-indole glyoxylic acid, methyl ester (7.07 g, 69%).
  • 6
  • [ 22980-09-2 ]
  • [ 124-41-4 ]
  • [ 18372-22-0 ]
YieldReaction ConditionsOperation in experiment
2.5 g In methanol; diethyl ether; at -78 - 20℃; To a solution of indole (2.0 g, 17.1 mmol) in Et2O (20 mL) was added oxalyl chloride (1.5 mL, 17.2 mmol) dropwise at 0 C. The yellow slurry was stirred at same temperature for 0.5 h and then cooled to -78 C. A solution of NaOMe in MeOH (25 wt %, 7.8 mL, 34.1 mmol) was added to this slurry at same temperature. After addition, the reaction mixture was allowed to warm to ambient temperature, and quenched by addition of H2O (10 mL). The precipitate was collected by filtration, washed with H2O and dried to give 12 (2.5 g, 73%) as a yellow solid: mp 160 C (dec.); 1H NMR (DMSO-d6) δ 12.42 (s, 1H), 8.45 (d, J = 3.5 Hz, 1H), 8.16 (dd, J = 1.5, 6.0 Hz, 1H), 7.55 (dd, J = 1.5, 6.0 Hz, 1H), 7.32-7.27 (m, 2H), 3.89 (s, 3H).
2.53 g In methanol; diethyl ether; at -78 - 20℃; To a stirred solution of indole (2.0 g, 17.1 mmol) in Et2O (20 mL) was added oxalyl chloride (1.5 mL,17.2 mmol) dropwise at 0 C. After the resultant yellow slurry was stirred at 0 C for 0.5 h, it was cooled to -78 C. A solution of NaOMe in MeOH (25 wt %, 7.8 mL, 34.1 mmol) was added to this slurry at -78 C. The reaction mixture was allowed to warm to room temperature and quenched by addition of water (10 mL). The solid was collected by filtration, rinsed with water and dried to give 4a (2.53 g, 73%) as a yellow solid
  • 7
  • [ 150114-41-3 ]
  • [ 18372-22-0 ]
  • [ 133052-89-8 ]
  • 9
  • [ 18372-22-0 ]
  • 1-(3-dimethylaminopropyl)indole-3-acetamide [ No CAS ]
  • [ 133052-90-1 ]
  • 10
  • [ 18372-22-0 ]
  • 1-(3-O'-triphenylmethylpropyl)indole-3-acetamide [ No CAS ]
  • [ 203719-61-3 ]
  • 11
  • [ 120-72-9 ]
  • [ 79-37-8 ]
  • [ 124-41-4 ]
  • [ 18372-22-0 ]
YieldReaction ConditionsOperation in experiment
90% A three-necked flask equipped with a magnetic stirrer and two addition funnels was charged with indole (10.1 g, 0.086 mol) and 100 mL of diethyl ether. Oxalyl chloride (7.3 mL, 0.086 mol) was added dropwise to the solution at 0 C under nitrogen in 0.5 h. Yellow precipitate were formed and the reaction mixture was stirred for another 0.5 h. The reaction mixture was cooled to -70 C by dry-ice, then sodium methylate (25 % solution in methanol, 37.3 g, 0.173 mol) was added dropwise to the reaction mixture in 1 h. After that the reaction mixture was warmed to 0 C and 50 mL of water was added. The precipitate were filtered, washed with water several times, and then dried at 60 C under vacuum. The product of methyl indolyl-3- glyoxylate was obtained as a yellow powder and used without further purification. Yield 90 %. A three-necked flask equipped with a magnetic stirrer and an addition funnel was charged with 3-indoleacetamide (8.0 g, 0.046 mol), methyl indolyl-3-glyoxylate (10.0 g, 0.049 mol) and 80 mL of tetrahydrofuran. A solution of potassium tert-butoxide (15.2 g, 0.135 mol) in 130 mL of tetrahydrofuran was added dropwise to the reaction mixture at 0 C under nitrogen in 1.5 h. Then the reaction mixture was warmed to room temperature and stirred for 3 h. A solution of Hydrochloric acid (35 % in water, 64 mL) was added dropwise to the reaction mixture in 1 h. Then 200 mL of ethyl acetate and 100 mL of water were added and stirred for dissolving. The organic phase was separated, washed with water several times until neutral, and then washed with brine once, dried over anhydrous sodium sulfate. The sodium sulfate was filtered and the solution was concentrated. The product was crystallized by adding a 1:1 (v/v) mixture of ethyl acetate and n-hexane dropwise to the concentrated solution at 50~60 C. The pure product of 3,4-bisindolylmaleimide was obtained as a red crystal.
86.3% To a three-necked flask was added 3.0 g (0.026 mol) of indole,30 mL of anhydrous ether, stirring dissolved, control the temperature 0-5 oC,A solution of 3.4 g (0.026 mol) of oxalyl chloride in anhydrous ethyl ether (5 mL) was slowly added dropwise, followed by incubation for 1 h and then cooled to about -25 C,A solution of 16.3 g of sodium methoxide in methanol (17.5%, 0.052 mol)After dripping for 30 min, the reaction solution was poured into 100 mL of ice water, filtered, washed with water (3 x 10 mL)Dichloromethane (2 x 10 mL),Dried to give 4.5 g of a pale yellow solid 5a in a yield of 86.3%
86% To a solution of 1H-indole (6.00 g, 51.2 mmol, 1.00 equiv) in Et20(60.0 mL, 0.850 M) was added oxalyl chloride (5.27 mL, 61.4 mmol, 1.20equiv) dropwise at 0 C. The yellow slurry was stirred at 0 C for 30mm and then cooled to -78 C. A solution of NaOMe in MeOH (25%, 23.0mL) was added to this slurry at the same temperature. The reaction mixture was then allowed to warm up to room temperature, and was quenched by addition of water (40.0 ml) . The precipitate was collected by filtration, washed with water and dried to afford the title compoundas a gray solid (8.96 g, 44.0 mmol, 86% yield).NMR Spectroscopy: 1H NMR (700 MHz, (CD,)2S0, 25 C, 5): 12.50 (s, 1H),8.44 (d, J = 3.2 Hz, 1H), 8.16 (d, J = 7.6 Hz, 1H), 7.55 (d, J 7.7Hz, 1H), 7.25 - 7.33 (m, 2H), 3.89 (s, 3H) . “C NMR (175 MHz, (CD3)2S0,25 C, 5): 178.7, 164.0, 138.4, 136.7, 125.5, 123.8, 122.9, 121.1,112.8, 112.4, 52.5. The ‘H NMR data were in good agreement with values reported in the literature (Ye, Q. et al. 2015)
  • 14
  • [ 18372-22-0 ]
  • [ 6343-93-7 ]
  • 3-(1<i>H</i>-indol-3-yl)-4-(4-methoxy-phenyl)-pyrrole-2,5-dione [ No CAS ]
  • 15
  • [ 18372-22-0 ]
  • [ 74860-13-2 ]
  • 3-(4-bromo-phenyl)-4-(1<i>H</i>-indol-3-yl)-pyrrole-2,5-dione [ No CAS ]
  • 17
  • [ 18372-22-0 ]
  • [ 221377-36-2 ]
  • [ 221377-35-1 ]
  • 18
  • [ 120-72-9 ]
  • [ 67-56-1 ]
  • [ 79-37-8 ]
  • [ 18372-22-0 ]
YieldReaction ConditionsOperation in experiment
90% In a reaction flask,7 g ( 60 mmol ) indole and 300 mL of dry diethyl ether were add, and 16.1 mL of oxalyl chloride was added dropwise to the reaction solution at 0 C. The reaction was continued for 6 h at room temperature to form a yellow suspension. It was further placed at 0 C, 12 mL of methanol was added dropwise to the reaction, and the mixture was stirred for 30 min. The resulting mixture was filtered and washed with ice ether to finally obtain a yellow solid 1 ( 10.93 g , 90% yield).
90% 7g (60mmol) of indole and 300mL of dry ether were added to a reaction flask, and 16.1mL of oxalyl chloride was added dropwise to the reaction solution at 0C. After the drop was completed, the reaction was carried out at room temperature for 6 hours to form a yellow suspension. It was placed at 0 C., 12 mL of methanol was added dropwise thereto, and stirred for 30 min. The resulting mixture was filtered and washed with glacial ether. Finally, 10.93 g of yellow solid 1 was obtained with a yield of 90%.
To a solution of indole (10.0 mmol, 1.0 equiv) in dry Et2O (50 mL) was added dropwise oxalyl chloride (2.7 mL, 30.0 mmol, 3.0 equiv) at 0 C. Then the ice bath was removed and the resulting yellow slurry was stirred for 6 h at room temperature. The reaction mixture was then cooled to 0 C and quenched with MeOH (2.0 mL, 50.0 mmol, 5.0 equiv). The crude precipitate was collected by filtration and was washed with cold Et2O. The solid 3 was dried under vacuum and useddirectly for the next step without further purification.A solution of compound 3 in THF (20 mL) was added dropwise to a suspension of LiAlH4 (1.5 g, 4.0equiv) in THF (40 mL) at 0 C. The reaction mixture was stirred for 4 h at room temperature and quenched with H2O (1.5 mL), 10% aqueous NaOH (3.0 mL), and H2O (4.5 mL) slowly at 0 C. Thereaction mixture was then filtered and the filtrate was extracted with EtOAc. The combined organic layerswere dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude mixture was purified by flash column chromatography on silica gel (petroleum ether:EtOAc, v/v = 1:1) to give tryptophol 5 (1.3 g, 80% for two steps) as a yellow solid. NMR data were in consistent with thosereported.15
  • 20
  • [ 18372-22-0 ]
  • [ 76513-69-4 ]
  • [ 259752-98-2 ]
  • 21
  • [ 18372-22-0 ]
  • [ 203719-71-5 ]
  • [ 203719-73-7 ]
  • 24
  • [ 18372-22-0 ]
  • [ 86864-60-0 ]
  • [ 609826-34-8 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 50℃; for 4h; A mixture of Compound 1d (4.00 g, 19.7 mmol), Compound 1b (5.19 g, 21.7 mmol) and cesium carbonate (7.06 g, 21.7 mmol) in DMF (40 mL) was stirred at 50 C. for 4 h and then filtered. The filtrate was evaporated in vacuo and the residue was separated by flash column chromatography (EtOAc/heptane, 1:2) to give Compound 1e as a viscous oil. 1HNMR (CDCl3) δ 8.61 (m, 2H), 7.51 (m, 3H), 4.45 (t, J=5.1 Hz, 2H), 4.13 (m, 2H), 4.10 (s, 3H), 0.96 (s, 9H), 0.1 (s, 6H). ES-MS m/z 362 (MH+).
  • 25
  • [ 18372-22-0 ]
  • [ 65999-53-3 ]
  • 3-(1H-indol-3-yl)-4-(2-bromophenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • 26
  • [ 18372-22-0 ]
  • [ 27387-22-0 ]
  • 3-(1H-indol-3-yl)-4-(2-bromo-5-methoxyphenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • 27
  • [ 18372-22-0 ]
  • 2-bromo-1-naphthaleneacetamide [ No CAS ]
  • 3-(1H-indol-3-yl)-4-(2-bromo-1-naphthalenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • 28
  • [ 18372-22-0 ]
  • 1-bromo-2-naphthaleneacetamide [ No CAS ]
  • 3-(1H-indol-3-yl)-4-(1-bromo-2-naphthalenyl)-1H-pyrrole-2,5-dione [ No CAS ]
  • 29
  • [ 18372-22-0 ]
  • [ 98-09-9 ]
  • [ 704913-80-4 ]
  • 30
  • [ 18372-22-0 ]
  • C9H10N4 [ No CAS ]
  • 3,6-bis-(1<i>H</i>-indol-3-yl)-2<i>H</i>-[1,2,4]triazin-5-one [ No CAS ]
  • 3,5-bis-(1<i>H</i>-indol-3-yl)-1<i>H</i>-[1,2,4]triazin-6-one [ No CAS ]
 

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Indoles

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