51843-24-4|1-(5-Chloro-1H-indol-3-yl)ethanone| Ambeed

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Quality Control of [ 51843-24-4 ] Purity: 97% SDS Specification

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Product Details of [ 51843-24-4 ]

CAS No. :	51843-24-4
Formula :	C₁₀H₈ClNO
M.W :	193.63
SMILES Code :	CC(C1=CNC2=C1C=C(Cl)C=C2)=O
MDL No. :	MFCD07437837
InChI Key :	LEUBXJIHEAWOHZ-UHFFFAOYSA-N
Pubchem ID :	2762971

Safety of [ 51843-24-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 51843-24-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	53.5
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.76
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.36
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.02
Log P_o/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.	1.74
Log P_o/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	3.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.47

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.97
Solubility	0.206 mg/ml ; 0.00106 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.	-2.69
Solubility	0.395 mg/ml ; 0.00204 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	-4.24
Solubility	0.0112 mg/ml ; 0.0000578 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.81 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	1.0
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	0.0 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)	1.4

Application In Synthesis of [ 51843-24-4 ]

* 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 [ 51843-24-4 ]

[ 51843-24-4 ] Synthesis Path-Downstream 1~35

1
[ 70978-35-7 ]
[ 51843-24-4 ]
1-(5-chloro-1H-indol-3-yl)-3-hydroxy-3-[1-(4-methoxy-benzyl)-1H-tetrazol-5-yl]-propenone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3184 - 3194.

2
[ 17422-32-1 ]
[ 108-24-7 ]
[ 51843-24-4 ]

Yield	Reaction Conditions	Operation in experiment
79%	With yttrium(III) trifluoromethanesulfonate; at 100℃; for 0.166667h;Microwave irradiation; Ionic liquid; Green chemistry;	General procedure: A 10 mL glass vessel suited for the monomode microwave oven was charged with 1 mmol substrate,1 mmol acid anhydride, 0.01 mmol metal triflate, and 1 mmol ionic liquid. Next, the vessel was sealedwith a Teflon cap and irradiated in a monomode microwave oven at many different reaction conditions(temperature and time) to find the optimal condition. Upon completion, the vessel was cooled down toroom temperature and the mixture was extracted with Et2O (5 × 10 mL). The ether layer was decantedand washed with water (2 × 10 mL), saturated aqueous NaHCO3 (2 × 20 mL), and brine (2 × 10 mL).The organic layer was dried over MgSO4, filtered, and the solvent was removed by a rotary evaporator.The isolated yield was determined after purification by flash chromatography (silica gel, n-hexane/ethylacetate, gradient 10:0 to 8:2).
45%	With acetic acid; for 20h;Reflux;	A mixture of compound 5a (9.1 g, 0.06 mol), glacial acetic acid (9.1 mL) and acetic anhydride (91 mL) was heated to reflux for 20 h. Upon cooling to room temperature, the solid was collected by filtration and purified by silica gel column chromatography. 6a was obtained as a white solid (5.2 g, 45%). m.p. 246-247 C. ESI-MS m/z: 194.1 (Cl = 35), 196.0 (Cl = 37) [M + H]+. 1H NMR (300 MHz, DMSO-d6) delta: 2.44 (s, 3H), 7.23-7.19 (m, 1H), 7.49 (d, J = 9.0 Hz, 1H), 8.15 (d, J = 1.8 Hz, 1H), 8.37 (s, 1H).

References: [1]RSC Advances,2017,vol. 7,p. 54399 - 54406.
[2]Molecules,2015,vol. 20,p. 19605 - 19619.
[3]Journal of Medicinal Chemistry,2002,vol. 45,p. 3184 - 3194.
[4]European Journal of Medicinal Chemistry,2011,vol. 46,p. 3149 - 3157.
[5]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 793 - 801.

3
[ 95-92-1 ]
[ 51843-24-4 ]
4-(5-chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride; sodium; In tetrahydrofuran; ethanol;	(1) 4-(5-Chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid ethyl ester In 100 ml of EtOH was dissolved 2.99 g (126 mmol) of sodium under heating. The EtOH was evaporated under reduced pressure and the residue was suspended in THF (200 ml). The THF was evaporated. To the suspension of the residue in THF (124 ml) was added 18.1 g (124 mmol) of diethyl oxalate. Subsequently, to the above suspension was added at room temperature, 12 g (62 mmol) of <strong>[51843-24-4]3-acetyl-5-chloroindole</strong>. After stirring for 3 hours, the mixture was stirred at 50 C. for additional 16 hours. The solvent was removed under reduced pressure. The resulting residue was washed with ether, and added to 1N hydrochloric acid (120 ml). The precipitated crystal was collected by filtration, and washed with water and ethyl acetate. Then the crystal was purified by recrystallization from dioxane and dried at 80 C. under reduced pressure to give 14.7 g of the titled compound. Yield: 81%. m.p.: 219-225 C. (decomposition) NMR(d6-DMSO) delta: 1.32(3H, t, J=7.2 Hz), 4.31(2H, q, J=7.2 Hz), 7.03(1H, s),7.30(1H, dd, J=8.4 Hz, 2.1 Hz), 7.54(1H, d, J=8.4 Hz), 8.21(1H, d, J=2.1 Hz), 8.83(1H, s), 12.6(1H, s).

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3184 - 3194.
[2]Patent: US6333323,2001,B1 .

4
[ 17422-32-1 ]
[ 75-36-5 ]
[ 51843-24-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With silver perchlorate; niobium pentachloride; In dichloromethane; at 0 - 30℃; for 4.3h;	General procedure: In a round-bottom flask, an indole (153 mg, 1.3 mmol) was dissolved in a dry DCM (1.5 mL) at 0 C then the solution of acyl chloride (140 mg, 1 mmol) in DCM (1.5 mL) with syringe and 1 mol % of NbCl5 and 3 mol % of AgClO4 was added. The reaction temperature was then slowly increased to 30 C and the reaction was carried out at this constant temperature constantly. After 4 h the reaction was completed and monitored by TLC, then reaction mass was quenched by adding 5 mL water and extracted with ethyl acetate (2 x 15 mL). This subsequent extract was washed with water 10 mL, dried over anhydrous MgSO4 and evaported under vacuum. The purification of crude mass was done column chromatography on silica gel (100-200 mesh) by eluting with ethyl acetate and petroleum ether (10:90), which offered 3-benzoylindole (177 mg, 75 % yield) (Scheme-I). The yield of other indoles and acyl chlorides are given in Table-1.
		Take SnCl4 (20 mmol) in a flask, 15 mL of toluene was added and the mixture was stirred in an ice-water bath. To the system was added acetyl chloride (20 mmol). After stirring for 0.5 h in ice-water bath, 2 mL of toluene was dissolved in 5-chloroindole (l0mmol), Was added dropwise to the reaction system, and the ice-water bath was stirred for 2h. TLC monitoring reaction completely, vacuum distillation to remove toluene, water and ethyl acetate extraction, combined organic phase, anhydrous magnesium sulfate drying. The magnesium sulfate was removed by suction filtration, and the filtrate was concentrated to recrystallize from absolute ethanol to give Compound 3.

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.
[2]Asian Journal of Chemistry,2020,vol. 32,p. 317 - 321.
[3]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.
[4]Patent: CN107226810,2017,A .Location in patent: Paragraph 0065.
[5]ChemMedChem,2018,vol. 13,p. 1353 - 1362.
[6]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 702 - 707.

5
[ 100-39-0 ]
[ 51843-24-4 ]
[ 866941-27-7 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.
[2]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.
[3]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 793 - 801.

6
[ 459-46-1 ]
[ 51843-24-4 ]
[ 866941-28-8 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.
[2]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

7
[ 85118-00-9 ]
[ 51843-24-4 ]
[ 947589-63-1 ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

8
[ 870-63-3 ]
[ 51843-24-4 ]
C₁₅H₁₆ClNO [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 793 - 801.

9
[ 74-96-4 ]
[ 51843-24-4 ]
C₁₂H₁₂ClNO [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 793 - 801.

10
[ 75-30-9 ]
[ 51843-24-4 ]
C₁₃H₁₄ClNO [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 793 - 801.

11
[ 77-78-1 ]
[ 51843-24-4 ]
1-(5-chloro-1-methyl-1H-indol-3-yl)ethanone [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 793 - 801.

12
[ 51843-24-4 ]
4-(1-benzyl-5-chloro-1H-indol-3-yl)-2-hydroxy-4-oxo-but-2-enoic acid [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.

13
[ 51843-24-4 ]
4-(1-benzyl-5-chloro-1H-indol-3-yl)-2-hydroxy-4-oxo-but-2-enoic acid ethyl ester [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.

14
[ 51843-24-4 ]
4-[5-chloro-1-(4-fluoro-benzyl)-1H-indol-3-yl]-2-hydroxy-4-oxo-but-2-enoic acid [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.

15
[ 51843-24-4 ]
4-[5-chloro-1-(4-fluoro-benzyl)-1H-indol-3-yl]-2-hydroxy-4-oxo-but-2-enoic acid ethyl ester [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.
[2]Journal of Medicinal Chemistry,2005,vol. 48,p. 7084 - 7088.

16
[ 51843-24-4 ]
ethyl (Z)-4-[1-(2,6-difluorobenzyl)-5-chloro-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoate [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

17
[ 51843-24-4 ]
4-(1-benzyl-5-chloro-1H-indol-3-oyl)-3-hydroxyfuran-2(5H)-one [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

18
[ 51843-24-4 ]
4-[1-(4-fluorobenzyl)-5-chloro-1H-indol-3-oyl]-3-hydroxyfuran-2(5H)-one [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

19
[ 51843-24-4 ]
4-[1-(2,6-difluorobenzyl)-5-chloro-1H-indol-3-oyl]-3-hydroxyfuran-2(5H)-one [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

20
[ 51843-24-4 ]
(Z)-4-[1-(2,6-difluorobenzyl)-5-chloro-1H-indol-3-yl]-2-hydroxy-4-oxobut-2-enoic acid [ No CAS ]

References: [1]Archiv der Pharmazie,2007,vol. 340,p. 292 - 298.

21
[ 51843-24-4 ]
4-(5-chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3184 - 3194.

22
[ 51843-24-4 ]
1-(5-chloro-1H-indol-3-yl)-3-hydroxy-3-(1H-tetrazol-5-yl)-propenone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3184 - 3194.

23
2-trityl-2H-tetrazole-5-carboxylic acid ethyl ester [ No CAS ]
[ 51843-24-4 ]
1-(5-Chloroindol-3-yl)-3-hydroxy3-(2-trityl-2H-tetrazol-5-yl)-propenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate;	(1) 1-(5-Chloroindol-3-yl)-3-hydroxy3-(2-trityl-2H-tetrazol-5-yl)-propenone To a solution of 0.58 g (3.0 mmol) of <strong>[51843-24-4]3-acetyl-5-chloroindole</strong> in THF (9 ml) was added dropwise 1M LHMDS (9 ml, 9 mmol) in THF under -65 C. The mixture was warmed to -20 C., and stirred at the same temperature for 1 hour. After cooling down to -65 C., a solution of 1.73 g (4.5 mmol) of 2-trityl-2H-tetrazole-5-carboxylic acid ethyl ester in THF (3 ml) was added thereto. The reaction mixture was gradually warmed to room temperature and stirred for 2 hours. The reaction mixture was poured into excess amount of saturated aqueous ammonium chloride. The precipitated was collected by filtration and dissolved in THF (100 ml), and then dried. Furthermore, the aqueous layer was extracted twice with ethyl acetate. The ethyl acetate was washed with water, and dried. The combined solutions were concentrated and the resulting residue was washed with ethyl acetate to give 1.40 g of the titled compound as an yellow powder. Yield: 88%. NMR(d6-DMSO) delta: 6.66 (1H, s), 7.05-7.08 (5H, m), 7.14 (1H, dd, J=8.4 Hz, 2.1 Hz), 7.39-7.44 (11H, m), 8.01 (1H, s), 8.29 (1H, d, J=2.1 Hz), 11.7 (1H, brs).

References: [1]Patent: US6333323,2001,B1 .

24
[ 60-12-8 ]
[ 51843-24-4 ]
3-Acetyl-5-chloro-1-phenethylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran;	(1) To a mixture of 0.58 g (3 mmol) of <strong>[51843-24-4]3-acetyl-5-chloroindole</strong>, 1.42 g (5.4 mmol) of triphenylphosphine and 0.66 g (5.4 mmol) of phenethyl alcohol in THF (12 ml) was added under ice-cooling, 1.09 g (5.4 mmol) of diisopropyl azodicarboxylate. After stirring for 3 hours at room temperature, the mixture was concentrated under reduced pressure. The obtained residue was chromatographed on silica gel (1/4 ethyl acetate/toluene as eluant) to give 0.58 g of the titled compound as an oil. Yield: 65%. NMR(CDCl3) delta: 2.38(1H, s), 3.12(2H, t, J=7.2 Hz), 4.36(2H, t, J=7.2 Hz), 6.97-7.01(2H, m), 7.20-7.30(5H, m), 7.38(1H, s), 8.38(1H, d, J=1.8 Hz).

References: [1]Patent: US6333323,2001,B1 .

25
[ 10517-21-2 ]
[ 51843-24-4 ]