93247-78-0|Methyl 1H-indole-7-carboxylate| Ambeed

Structure of 93247-78-0

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Quality Control of [ 93247-78-0 ] Purity: 97% SDS Specification

COA

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NMR

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Product Details of [ 93247-78-0 ]

CAS No. :	93247-78-0
Formula :	C₁₀H₉NO₂
M.W :	175.18
SMILES Code :	C1=CC=C2C(=C1C(OC)=O)[NH]C=C2
MDL No. :	MFCD00211064
InChI Key :	FTLOEULOTNVCGF-UHFFFAOYSA-N
Pubchem ID :	676694

Safety of [ 93247-78-0 ]

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

Computational Chemistry of [ 93247-78-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.1
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	49.58
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	42.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.04
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	1.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.95
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.	1.38
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	2.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.93

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.5
Solubility	0.55 mg/ml ; 0.00314 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.	-2.41
Solubility	0.687 mg/ml ; 0.00392 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	-3.36
Solubility	0.0772 mg/ml ; 0.000441 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.	-6.02 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)	1.29

Application In Synthesis of [ 93247-78-0 ]

* 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 [ 93247-78-0 ]

[ 93247-78-0 ] Synthesis Path-Downstream 1~54

1
[ 93247-78-0 ]
[ 1074-87-9 ]

Yield	Reaction Conditions	Operation in experiment
98%		Example 1 Preparation of P001 Indole-7 carboxyldehyde (I-1). Ethyl Indole-7 m carboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. Vol IIV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in 250 ml of anhydrous THF was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2 h. After cooling to room temperature, the excess hydride was quenched by addition of water (12 mL), 15percent NaOH (12 mL) and water (26 mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (1H-indol-7-yl)-methanol (10.7 g, 98percent). 1H-NMR (CDCl3).
98%		Example 17; Preparation of Al3; Indole-7 carboxyldehyde (K-44); Methyl 7-indolecarboxylate was prepared according to literature procedure {Batcho B. and Leimgruber, K., Org. Syn. VoI HV, page 34-40). To a solution of methyl 7-indolecarboxylate (13 g, 74.2 mmol) in anhydrous THF (250 niL) was added LiAlH4 (10.9 g, 0.288 mol) in portions, and reaction mixture was heated to reflux for 2h. After cooling to room temperature, the excess hydride was quenched by addition of water (12mL), 15percent NaOH (12mL) and water (26mL). The solids were removed by filtration through a pad of Celite and filtrate was evaporated in vacuo to yield (lH-indol-7-yl)- methanol (10.7 g, 98percent). 1HNMR (CDCl3). To a solution of the alcohol, (IH- indol-7-yl)-methanol (8.0 g, 54.3 mmol) in 400 mL of methylene chloride was added activated manganese (IV) oxide (85percent, 41.0 g, 0.40 mol), and stirred at ambient temperature for 72h. After additional of 200 mL of methylene chloride and 400 mL of methanol to the reaction mixture, the whole mixture was filtered through a pad of silica gel to remove solid materials. The filtrate was concentrated to afford a crude product, which was purified by a column chromatography on silica gel to yield lH-indole-7-carbaldehyde, K-44 (6.55 g, 83percent).
	With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane;	iii) 7-Indole methanol Solid lithium aluminum hydride (1.0 g) was added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.

	With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane;	Part C Preparation of 7-Indole Methanol Solid lithium aluminum hydride (1.0 g) is added in portions over 1 hour to a stirred solution of methyl 7-indolecarboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminum hydride was destroyed by addition of acetic acid, the mixture is diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract is dried and evaporated and the residue is chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.
	With acetic acid; In tetrahydrofuran; ethyl acetate n-hexane;	iii) 7-Indole methanol Solid lithium aluminium hydride (10 g) was added in portions over 1 hour to a stirred solution of methyl 7-indole-carboxylate (6.7 g) in tetrahydrofuran (100 ml). The mixture was stirred for a further 2 hours then excess lithium aluminium hydride was destroyed by addition of acetic acid, the mixture was diluted with aqueous sodium hydroxide and extracted with ethyl acetate. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:9 to 1:2) to give the product.

References: [1]Patent: US2006/79520,2006,A1 .Location in patent: Page/Page column 43.
[2]Patent: WO2006/44415,2006,A2 .Location in patent: Page/Page column 78; 106-107.
[3]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.
[4]Patent: US5281593,1994,A .
[5]Patent: US5486612,1996,A .
[6]Patent: EP469833,1992,A1 .

2
[ 68109-89-7 ]
[ 93247-78-0 ]

Yield	Reaction Conditions	Operation in experiment
	palladium on charcoal; In toluene;	ii) Methyl 7-indolecarboxylate A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]-2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) was hydrogenated at 60 psi over 10percent palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica to give the product.
	palladium on charcoal; In toluene;	Part B Preparation of Methyl 7-indolecarboxylate A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]-2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) is hydrogenated at 60 psi (4.22 Kg/cm2) over 10percent palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst is filtered off, the filtrate is evaporated and the residue is chromatographed on silica to give the product.
	palladium on charcoal; In toluene;	ii) Methyl 7-indolecarboxylate A solution of methyl 3-[2-(E)-(dimethylamino)ethenyl]- 2-nitrobenzoate (12.0 g, 48 mmol) in toluene (200 ml) was hydrogenated at 60 psi over 10percent palladium on charcoal (1.5 g) until hydrogen uptake ceased. The catalyst was filtered off, the filtrate was evaporated and the residue was chromatographed on silica to give the product.

References: [1]Journal of Heterocyclic Chemistry,1985,vol. 22,p. 121 - 125.
[2]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.
[3]Patent: US5281593,1994,A .
[4]Patent: US5486612,1996,A .
[5]Patent: EP469833,1992,A1 .

3
[ 5471-82-9 ]
[ 4637-24-5 ]
[ 93247-78-0 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.

4
[ 126759-45-3 ]
[ 93247-78-0 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1405 - 1413.

5
[ 50-00-0 ]
[ 93247-78-0 ]
[ 124-40-3 ]
[ 312915-01-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

6
[ 51417-51-7 ]
[ 79-22-1 ]
[ 93247-78-0 ]

References: [1]Synthetic Communications,1997,vol. 27,p. 2033 - 2039.

7
[ 100-39-0 ]
[ 93247-78-0 ]
[ 189634-92-2 ]

References: [1]Synthetic Communications,1997,vol. 27,p. 2033 - 2039.

8
[ 126759-37-3 ]
[ 93247-78-0 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5838 - 5845.
[2]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1405 - 1413.

9
[ 67-56-1 ]
[ 51417-51-7 ]
[ 201230-82-2 ]
[ 93247-78-0 ]

References: [1]Organic Letters,2006,vol. 8,p. 2167 - 2170.

10
[ 93247-78-0 ]
[ 74-88-4 ]
[ 167479-21-2 ]

Yield	Reaction Conditions	Operation in experiment
		(Intermediate Example 33) 1-Methyl-1H-indole-7-carboxylic acid Methyl 1H-indole-7-carboxylate (546 mg) was dissolved in N,N-dimethylformamide (8 ml) and cooler to 0C. Sodium hydride (370 mg) was added thereto and stirred as such for 30 minutes. Methyl iodide (0.38 ml) was added slowly dropwise thereto, and the mixture was warmed to room temperature and stirred for 2 hours. The mixture was diluted with ethyl acetate, and the organic phase was washed with 2 N hydrochloric acid, a saturated sodium bicarbonate solution and a saturated saline solution. The resulting product was dried over sodium sulfate anhydrous and then concentrated under reduced pressure. 1,4-Dioxane (14 ml) and 1 N sodium hydroxide solution (14 ml) were added to the above compound and stirred for 17 hours at 40C. The mixture was acidified by 2 N hydrochloric acid and extracted with chloroform. The extract was dried over sodium sulfate anhydrous and then concentrated under reduced pressure. Precipitates were collected by filtration, washed with n-hexane and dried under reduced pressure to give the title compound (296 mg, Y.: 55%). 1H NMR; (DMSO-d6) delta (ppm): 3.8 (1H, s), 6.5 (1H, d), 7.1 (1H, t), 7.4 (1H, d), 7.5 (1H, dd), 7. 7 (1H, dd). ESI/MS (m/z): 176 (M+H)+, 174 (M-H)-.

References: [1]Heterocycles,2006,vol. 67,p. 643 - 653.
[2]Patent: EP1595866,2005,A1 .Location in patent: Page/Page column 18.
[3]Organic Letters,2019,vol. 21,p. 1139 - 1143.

11
[ 93247-78-0 ]
[ 402-23-3 ]
[ 955039-52-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃; for 0.5h;	Step 1 : methyl l-[3-(trifluoromethyl)benzyl]-lH-indole-7-carboxylate; Methyl lH-indole-7-carboxylate (Ig, 5.71mmol) and l-(bromomethyl)-3-(trifluoromethyl)benzene (956ul, 6.28mmol) were dissolved in DMF (16ml), in an ice bath. 60percent w/w NaH (251mg, 6.28mmol) was added portionwise. The ice bath was removed and the mixture stirred at RT for 30min. The reaction mixture was quenched with NH4Cl(SaL) and <n="24"/>extracted 3 times with ether. The organic layers were combined, washed with water and brine. The compound was purified by flash chromatography on silica gel. IH NMR (500 MHz, DMSO- d6): delta 7.40 (d, IH), 7.25 (s, IH), 7.10 (m, IH), 7.00 (m, 2H), 6.75 (s, IH), 6.65 (t, IH), 6.50 (d, IH), 6.25 (s, IH), 5.25 (s, 2H), 2.05 (d, 3H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3760 - 3763.
[2]Patent: WO2007/121578,2007,A1 .Location in patent: Page/Page column 22-23.

12
[ 625-99-0 ]
[ 93247-78-0 ]
methyl 1-(3-chlorophenyl)-1H-indole-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; 2,2,6,6-tetramethylheptane-3,5-dione; at 120℃; for 72h;	Step 1 Methyl 1 -(3 -chlorophenyl)- 1 H- indole-7-carboxylate; A mixture of methyl lH-indole-7-carboxylate (0.175 g), 3-iodo-chlorobenzene (0.358 g), Cs2CO3 (0.490 g), CuCl (0.099 g), and 2,2,6,6-tetramethyl-3,5-heptanedione (0.04 mL) in 5 mL of N-methylpyrolidine was heated at 120 0C for 3 days. The mixture was then diluted with 50 mL of EtOAc and filtered through a pad of solica gel. The filtrate was washed with 3 x 15 mL of water and dried over Na2SO4. After filtration and concentration, the residue was purified by Combiflash eluted with a gradient of EtOAc/hexane to give 0.1 g of the title compound.IH NMR (500 MHz, Acetone-d6): delta 7.90 (d, IH), 7.58 (d, IH), 7.50-7.58 (m, 2H), 7.41-7.46 (m, 2H), 7.23 (d, IH), 7.25 (t, IH), 6.83 (s, IH).

References: [1]Patent: WO2007/121578,2007,A1 .Location in patent: Page/Page column 25.

13
[ 93247-78-0 ]
indole-7-isocyanate [ No CAS ]

References: [1]Heterocycles,2006,vol. 67,p. 643 - 653.

14
[ 93247-78-0 ]
1-methyl-1<i>H</i>-indole-7-carbonyl azide [ No CAS ]

References: [1]Heterocycles,2006,vol. 67,p. 643 - 653.

15
[ 93247-78-0 ]
[ 167479-16-5 ]

References: [1]Heterocycles,2006,vol. 67,p. 643 - 653.

16
[ 577-19-5 ]
[ 93247-78-0 ]

References: [1]Organic Letters,2006,vol. 8,p. 2167 - 2170.

17
[ 5471-82-9 ]
[ 93247-78-0 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5838 - 5845.
[2]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

18
[ 132874-06-7 ]
[ 93247-78-0 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5838 - 5845.

19
(3-Methoxycarbonyl-2-nitro-benzyl)-triphenyl-phosphonium; bromide [ No CAS ]
[ 93247-78-0 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5838 - 5845.

20
[ 93247-78-0 ]
2-Benzyl-1H-indole-7-carboxylic acid methyl ester [ No CAS ]

References: [1]Synthetic Communications,1997,vol. 27,p. 2033 - 2039.

21
[ 5437-38-7 ]
[ 93247-78-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

22
[ 93247-78-0 ]
[ 1026370-09-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

23
[ 93247-78-0 ]
[ 1028271-58-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

24
[ 93247-78-0 ]
1-(2-Chloro-ethyl)-3-imidazol-1-ylmethyl-1H-indole-6-carboxylic acid methyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

25
[ 93247-78-0 ]
1-(4-Chloro-butyl)-3-imidazol-1-ylmethyl-1H-indole-6-carboxylic acid methyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

26
[ 93247-78-0 ]
[ 1027073-83-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

27
[ 93247-78-0 ]
1-[2-(4-Benzhydryl-piperazin-1-yl)-ethyl]-3-imidazol-1-ylmethyl-1H-indole-6-carboxylic acid methyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

28
[ 93247-78-0 ]
1-[4-(4-Benzhydryl-piperazin-1-yl)-butyl]-3-imidazol-1-ylmethyl-1H-indole-6-carboxylic acid methyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

29
[ 93247-78-0 ]
Sodium; 1-[3-(4-benzhydryl-piperazin-1-yl)-propyl]-3-imidazol-1-ylmethyl-1H-indole-7-carboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

30
[ 93247-78-0 ]
Sodium; 1-[2-(4-benzhydryl-piperazin-1-yl)-ethyl]-3-imidazol-1-ylmethyl-1H-indole-6-carboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

31
[ 93247-78-0 ]
Sodium; 1-[4-(4-benzhydryl-piperazin-1-yl)-butyl]-3-imidazol-1-ylmethyl-1H-indole-6-carboxylate [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 1692 - 1695.

32
[ 93247-78-0 ]
[ 1074-88-0 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.

33
[ 93247-78-0 ]
[ 104682-97-5 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.

34
[ 93247-78-0 ]
[ 111168-55-9 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.

35
[ 93247-78-0 ]
[ 111168-45-7 ]

References: [1]Chemical and pharmaceutical bulletin,1986,vol. 34,p. 4116 - 4125.

36
[ 104670-71-5 ]
[ 93247-78-0 ]

References: [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1405 - 1413.

Yield	Reaction Conditions	Operation in experiment
		C. 1H-Indole-7-carboxylic acid, methyl ester The title B semicarbazone (6.53 g, 23.3 mmol) was suspended in ethanol (50 ml), treated with 10percent palladium on carbon (1.3 g, 20percent by weight) and hydrogenated on a Parr shaker at up to 55 psi for six hours. The catalyst was removed by filtration through regenerated cellulose and the filtrate was dried in vacuo. The remaining material was purified by chromatography on silica gel eluding with chloroform:hexane (1:4 followed by 1:3) to give the title C compound (2.30 g) as white crystalline material.

38
petroleum [ No CAS ]
[ 124993-41-5 ]
[ 93247-78-0 ]
[ 150235-46-4 ]

Yield	Reaction Conditions	Operation in experiment
		i 1-[4-(Quinolin-2-ylmethoxy)benzyl]<strong>[93247-78-0]indole-7-carboxylic acid methyl ester</strong> This compound was prepared from methyl 7-indole carboxylate and 4-(quinolin-2-ylmethoxy)benzyl chloride (Example 1a) by the method described in Example 1b, part i. The residue was purified by chromatography on flash silica using petroleum spirit 40°-60° C./diethyl ether (2:1, 7:5) as eluent.

References: [1]Patent: US5410061,1995,A .

39
[ 93247-78-0 ]
[ 112106-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In 1,4-dioxane; water;	EXAMPLE 6 (Preparation of starting material) STR15 1.75 g of <strong>[93247-78-0]indole-7-carboxylic acid methyl ester</strong> and 2.92 g of borane-trimethylamine complex are dissolved in 10 ml of dioxane. To the resulting solution, 2 ml of concentrated hydrochloric acid are added. The reaction solution is heated under reflux for 30 minutes, and then cooled to room temperature. 10 ml of 6N hydrochloric acid are added to the reaction solution, which is then refluxed under heating for 15 minutes, and thereafter cooled to room temperature. The reaction solution is poured into 50 ml of water. The resulting mixture is neutralized with a 2N aqueous sodium hydroxide solution, and then extractd with ether. The organic layer is washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent has been distilled off, 1.26 g of 2,3-dihydro<strong>[93247-78-0]indole-7-carboxylic acid methyl ester</strong> are obtained, mp. 70° to 73° C.

References: [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 1341 - 1349.
[2]Patent: US4729998,1988,A .

40
[ 5470-11-1 ]
[ 93247-78-0 ]
[ 443144-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In N-methyl-acetamide;	2.1. Methyl 3-cyanoindole-7-carboxylate 9.1 g of phosphoryl chloride are added to 30 ml of dimethylformamide with ice cooling at a reaction temperature of 20-30°. A solution of 8 g of <strong>[93247-78-0]methyl indole-7-carboxylate</strong> in dimethylformamide is added dropwise, during which the temperature rises to 40°. After one hour at 125°, the solution is added dropwise while still hot to a solution of 6.3 g of hydroxylammonium chloride in 40 ml of dimethylformamide, and the mixture is stirred at 120° C. for a further 15 minutes. The mixture is poured into water, extracted with ethyl acetate, filtered through neutral aluminium oxide and evaporated, giving 4.5 g of methyl 3-cyanoindole-7-carboxylate having a melting range of 212-213.5° (48.9percent of theory).

References: [1]Patent: US2004/63723,2004,A1 .

41
[ 87-48-9 ]
[ 93247-78-0 ]
[ 1027787-84-3 ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In ethanol; at 20℃; for 48 - 96h;	Example 39 Preparation of QR-0303 and QR-0289[00386] Compounds QR-0303 and QR-0289 were prepared by reactions depicted in Scheme 45 below. <n="120"/>Scheme 45[00387] The procedure was as follows.[00388] A solution of 5-substituted isatin (5 mmol), indole-7-carboxylic acidmethyl ester (5 mmol), and piperidine (0.5 mmol) were stirred in ethanol at roomtemperature for 2-4 d. When TLC indicated the reaction was complete, the reactionmixture was concentrated and the product washed with EtOAc and hexane. Theproduct was used in the next step without further purification. To a solution of theproduct (4 mmol) in dry THF at O0C was added BH3-THF (10 mL, 10 mmol)dropwise over 10 min. The solution was stirred at room temperature overnight, andthen quenched by the dropwise addition of MeOH (30 mL). The solvent wasremoved under vacuum, giving crude product which was stirred with LiOH (10 mmol) in MeOHZH2O ( 1 : 1 , 40 mL) at 70 0C for 2h. The mixture was concentrated and the pH adjusted to 2 with IN HCl. The aqueous layer was extracted with EtOAc (2 x 20 mL) and the organic layer dried with MgSO4. Final product was purified by flash column chromatography to yield the following compounds.[00389] QR-0303 (32percent yield). 1H NMR (DMSO): 7.19 (t, I H. J=7.7), 7.28(d, I H, J=8.6), 7.45 (d, I H, J=8.6), 7.62 (d, I H, J=2.3). 7.76 (d, I H. J=2.3), 7.79 (d. <n="121"/>111..1=1.7).7.83 (d. IH, J=8.6), 8.02 (d, IH. J=7.8).11.15 (s, IH), 11.49 (s, IH), 13.12 (s, IH); 13C NMR (DMSO): 109.09, 109.79, 112.07, 114.15, 114.22, 119.05.121.74, 123.96, 124.30, 124.57, 124.78, 125.40.128.13, 128.33, 135.53, 135.55, 168.47.[00390] QR-0289 (27percent yield). 1H NMR (DMSO): 3.76 (s, 3H), 6.82 (d. IH,J=8.7), 7.14 (d, IH. J=2.0), 7.19 (t, IH, J=7.6).7.36 (d, IH, J=8.7), 7.60 (d, IH,J=2.2).7.63 (d, IH, J=2.2), 7.82 (d, IH, J=7.3), 8.03 (d, 1H,J=7.8), 11.11 (s, 2H), 13.10 (s, IH); 13C NMR (DMSO): 55.82, 101.60.109.10, 110.72, 111.83, 112.81, 114.13, 118.85.123.58, 123.62, 124.64.125.54.126.87.128.31.132.06.135.56,153.97,168.52.

References: [1]Patent: WO2008/58402,2008,A1 .Location in patent: Page/Page column 118-120.

42
[ 93247-78-0 ]
[ 402-49-3 ]
[ 1050656-28-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred solution of lH-Indole-7-carboxylic acid methyl ester 1 (209.8 g, 1.20 mole) in DMF (1.4 L) at 9 0C was added KOtBu (161.6 g, 1.44 mole) portion wise (temperature rose to 15 0C). The cold bath was removed and the reaction mixture was stirred at r.t. for 2 hours. The reaction mixture was cooled to 10 0C and a solution of l-bromomethyl-4-trifluoromethyl-benzene 2 (343.7g, 1.44 mole) in DMF (400 mL) was added over 2.5 hours and the flask was rinsed with DMF (100 mL). H2O (1.9 L) was added at 15 0C in order to precipitate the product. The slurry was filtered and rinsed with H2O (4 X IL) and the product dried under a flow of N2 under vacuum. 411.1 g of material was obtained at 82 A%. A sample was purified by chromatography : 1H NMR (500 MHz, Acetone-/) delta 7.88 (dd, J = 7.8, 1.1 Hz, IH), 7.60 (d, J = 8.2 Hz, IH), 7.58 (d, J = 3.2 Hz, IH), 7.53 (dd, J= 7.5, 1.1 Hz, IH), 7.13 (X, J = 7.6 Hz, IH), 7.07 (d, J = 8.0 Hz, IH), 6.74 (d, J = 3.2 Hz, IH), 5.83 (s, 2H), 3.72 (s, 3H); 19F NMR (377 MHz, Acetone-afe) delta - 62.4; 13C NMR (100 MHz, Acetone-tf6) delta 167.7, 143.8, 132.8, 132.7, 132.2, 128.9 (q, J= 32 Hz), 127.3, 126.0, 125.5 (m), 124.9, 123.3, 119.0, 117.4, 102.8, 52.2, 51.8; IR (CDCl3) 3112, 3076, 3038, 2987, 2949, 2844, 1925, 1716, 1619, 1524, 1448, 1421, 1321, 1275, 1161, 1134, 1113, 1067, 1017, 844, 749, 731cm"1; HRMS-ESI (m / z): [M+H]+ calcd for Ci8H14F3NO2, 334.10494; found 334.10548
	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20℃;	EXAMPLE 34- { 1 -[( { 1 - [4-(trifluoromethyl)benzyl] - 1 H-indol-7-yl } carbonyl)amino]cyclopropyl } benzoic acidStep 1 : Methyl l-[4-(trifluoromethyl)benzyl]-lH-indole-7-carboxylateMethyl lH-indole-7-carboxylate (47.8 g, 273 mmol) and l-(bromomethyl)-4- (trifluoromethyl)benzene (81 g, 341 mmol) were dissolved in DMF (1.3 L) at O0C. 60% w/w NaH (12 g, 300 mmol) was added portion wise. The ice bath was removed and the mixture stirred at O0C for 3 hours, then overnight at RT. The reaction mixture was quenched with 3 L of NH4Cl(sat.) and the aqueous layer was extracted 3 times with 1 L of ether. The organic layers were combined, washed with water and brine. The compound was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d): delta 8.90 (d, IH), 7.70 (s, IH), 7.60 (d, 2H), 7.40 (d, IH), 7.10 (t, IH), 7.00 (d, 2H), 6.70 (d, IH), 5.70 (s, 2H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3760 - 3763.
[2]Patent: WO2010/121382,2010,A1 .Location in patent: Page/Page column 9; 10.
[3]Patent: WO2008/104055,2008,A1 .Location in patent: Page/Page column 28.

43
[ 93247-78-0 ]
[ 824-94-2 ]
[ 1097196-82-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (100 mg) and DMF, (1 mL) was added potassium tert-butoxide (75 mg) at room temperature, followed by stirring for 5 minutes, and then 4-methoxybenzyl chloride (91 muL) was added thereto, followed by stirring at room temperature for 2 hours. Then, water and ethyl acetate were added thereto, and the separated organic layer was washed with water and saturated saline in this order, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain a residue (216 mg). To the obtained residue were added THF (10 mL), methanol (5 mL), and a 1 M aqueous sodium hydroxide solution (2.5 mL), followed by stirring at 60°C overnight. After leaving it to be cooled, to the residue obtained by concentration under reduced pressure was added ethyl acetate, followed by extraction with water. To the aqueous layer were added ethyl acetate and 1 M hydrochloric acid (2.5 mL), and the separated organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1-(4-methoxybenzyl)-1H-indole-7-carboxylic acid (157 mg) as a pale yellow solid.

References: [1]Patent: EP2172447,2010,A1 .Location in patent: Page/Page column 16.

44
[ 93247-78-0 ]
[ 622-95-7 ]
[ 1097196-86-5 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[93247-78-0]methyl indole-7-carboxylate</strong> (6.0 g) and DMF (60 mL) was ice-cooled, and potassium tert-butoxide (5.38 g) was added thereto, followed by stirring at the same temperature for 30 minutes. Then, 4-chlorobenzylbromide (7.39 g) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was ice-cooled, and water (60 mL) was added thereto, followed by extraction with ethyl acetate (80 mL). The organic layer was washed with 1 M hydrochloric acid, a saturated sodium bicarbonate solution, and saturated saline in this order, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was left to stand for 3 days for solidification, and washed with hexane-ethyl acetate (8:1, 18 mL) to obtain methyl 1-(4-chlorobenzyl)-1H-indole-7-carboxylate (4.94 g) as a pale yellow solid.

References: [1]Patent: EP2172447,2010,A1 .Location in patent: Page/Page column 17.

45
[ 93247-78-0 ]
[ 1097196-77-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With N-Bromosuccinimide; In tert-butyl alcohol; at 20℃; for 2h;Inert atmosphere;	(The title compound was prepared according to the procedure of Nozawa, Eisuke et al from PCT Int. Appl., 2009005076, 8 Jan. 2009.) To a mixture of methyl 1H-in-dole-7-carboxylate (6.00 g, 34.25 mmol) and tert-butanol (300 mE) was added N-bromosuccinimide (3.30 g, 18.5 mmol) portionwise at room temperature. This solution was stirred for 2 h at room temperature. The reaction mixture was concentrated under reduced pressure. To the residue wasadded a saturated sodium bicarbonate solution followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The crude product was purified by flash colunm chromatography to give the title compound (4.2 g,48percent).
	With N-Bromosuccinimide; In tert-butyl alcohol; at 20℃; for 2h;	To a mixture of <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (2.00 g) and tert-butanol (100 mL) was slowly added N-bromosuccinimide (1.10 g) at room temperature, followed by stirring for 1 hour. Additionally, N-bromosuccinimide (2.20 g) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and then to the residue was added a saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 3-bromo-1H-indole-7-carboxylate (490 mg) as a white solid.

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 13004 - 13009.
[2]Patent: US9464065,2016,B2 .Location in patent: Page/Page column 56.
[3]Patent: EP2172447,2010,A1 .Location in patent: Page/Page column 16.

46
[ 886503-33-9 ]
[ 93247-78-0 ]
C₁₈H₁₃ClF₃NO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3760 - 3763.

47
[ 93247-78-0 ]
[ 766-80-3 ]
C₁₇H₁₄ClNO₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3760 - 3763.

48
[ 33797-51-2 ]
[ 93247-78-0 ]
[ 312915-01-8 ]

Yield	Reaction Conditions	Operation in experiment
		lH-Indole-7-carboxylic acid, methyl ester (0.091 mol), Eschenmoser's salt (0.1 mol) in acetic acid (300 ml) were heated at 650C for 2 hours. The precipitate was filtered off, dissolved in DCM and potassium carbonate 10percent. Potassium carbonate (solid) was added and the mixture was stirred at room temperature for 1 hour and then extracted. The organic layer was separated, dried over MgSO4, filtered and the solvent was evaporated, yielding 1Og of intermediate 5.

References: [1]Patent: WO2010/89327,2010,A2 .Location in patent: Page/Page column 42.

49
[ 93247-78-0 ]
[ 68-12-2 ]
[ 312973-24-3 ]

Yield	Reaction Conditions	Operation in experiment
93%		To a stirred mixture of phosphorus oxychloride-dimethylformamide in anhydrous 1,2-dichloroethane (prepared by the slow addition of phosphorus oxychloride (0.43 ml, 4.6 mmol) to anhydrous DMF (0.35 ml, 4.6 mmol) in anhydrous 1,2-dichloroethane (6 ml) cooled below 5° C.) a solution of 7-methoxycarbonylindole (0.69 g, 4 mmol) in anhydrous 1,2-dichloroethane (6 ml) was dropwise below 5° C. The mixture was stirred at room temperature for 2 h and then was heated at 50° C. for 30 minutes. After cooling, the precipitate was filtered off and washed with 1,2-dichloroethane. This precipitate was suspended in aq Na2CO3 10percent (30 ml) and stirred at room temperature for 20 minutes; dichloromethane was added and stirring was continued 10 minutes more. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated to yield 0.75 g (93percent) of the entitled product. Mp: 153-4° C.

References: [1]Patent: US7049312,2006,B1 .Location in patent: Page/Page column 112.
[2]Chemistry - A European Journal,2016,vol. 22,p. 13004 - 13009.

50
[ 93247-78-0 ]
[ 17201-43-3 ]
[ 1196052-11-5 ]

Yield	Reaction Conditions	Operation in experiment
75%		To a solution of <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (1 eq.) in DMF (0.29 M) cooled to 0°C was added potassium tert-butoxide (1.2 eq.) such that the reaction temperature does not exceed 5°C. The resulting suspension was stirred at 0°C for 30 mm and then at RT for 30 mm. The solution was re-cooled to 0°C and 4-(bromomethyl)benzonitrile (1.2 eq.) in DMF (0.69M) was added dropwise. The reaction mixture was allowed to warm slowly to RT over 16 h and then quenched with the addition of ice-water and extracted with EtOAc. The combined organic extracts were washed further with water, 10percent aq. NaHCO3 and brine, dried over Mg504, and filtered. Concentration of the filtrate in vacuo furnished the crude reaction product as a yellow viscous oil, which was purified by column chromatography (5i02, gradient elution, 9:1 Hexane/EtOAc to EtOAc) to afford the product as a colorless oil that solidified upon standing (75percent yield).
		Production Example 6; To a mixture of <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (100 mg) and DMF (1 mL) was added potassium tert-butoxide (75 mg) at room temperature, followed by stirring for 5 minutes. To the reaction mixture was added 4-(bromomethyl)benzonitrile (131 mg), followed by stirring at room temperature for 2 hours. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain crude methyl 1-(4-cyanobenzyl)-1H-indole-7-carboxylate (211 mg). To a mixture of crude methyl 1-(4-cyanobenzyl)-1H-indole-7-carboxylate (211 mg), THF (10 mL), and methanol (5 mL) was added a 1 M aqueous sodium hydroxide solution (2.5 mL), and the obtained mixed liquid was stirred at 60°C overnight. After leaving to be cooled to room temperature, the solvent was evaporated under reduced pressure, and to the obtained residue was added ethyl acetate, followed by extraction with water. The aqueous layer was neutralized by adding 1 M hydrochloric acid (2. mL), and extracted with ethyl acetate. This organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated to obtain crude 1-(4-carbamoylbenzyl)-1H-indole-7-carboxylic acid (230 mg). To a mixture of crude 1-(4-carbamoylbenzyl)-1H-indole-7-carboxylic acid (229 mg), methyl (S)-4-[1-aminoethyl]benzoate hydrochloride (123 mg), and HOBt (23 mg) in DMF (3 mL) was added EDCI-HCl (150 muL), followed by stirring at room temperature for 3 hours. Water was added thereto, followed by extraction with ethyl acetate-diethyl ether. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After evaporating the solvent, to the obtained residue was added ethanol. The precipitated solid was collected by filtration and dried to obtain methyl (S)-4-[1-([1-(4-carbamoylbenzyl)-1H-indol-7-yl]carbonyl}amino)ethyl]benzoate (142 mg).

References: [1]Patent: WO2018/195123,2018,A1 .Location in patent: Paragraph 00236.
[2]Patent: EP2277858,2011,A1 .Location in patent: Page/Page column 24.

51
[ 690631-99-3 ]
[ 93247-78-0 ]
[ 1196047-33-2 ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 55 To (6-piperidin-1-ylpyridin-3-yl)methanol (0.61 g) was added methylene chloride (6.0 mL), and thionyl chloride (1.0 mL) was added dropwise thereto under ice-cooling. In addition, a catalytic amount of DMF was added thereto, followed by stirring at room temperature for 2 hours. Methylene chloride (5.0 mL) and thionyl chloride (1.0 mL) were added thereto, followed by stirring at 60°C overnight. The reaction mixture was concentrated under reduced pressure, and DMF (10 mL) was added thereto. Then, <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (0.56 g) and potassium tert-butoxide (1.3 g) were added thereto under ice-cooling, followed by stirring at room temperature for 3 hours. The reaction mixture was extracted by adding ethyl acetate and water, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, then filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5-70/30) to obtain methyl 1-[(6-piperidin-1-ylpyridin-3-yl)methyl]-1H-indole-7-carboxylate (0.12 g).

References: [1]Patent: EP2277858,2011,A1 .Location in patent: Page/Page column 33.

52
[ 2567-29-5 ]
[ 93247-78-0 ]
[ 1196047-31-0 ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 53 To <strong>[93247-78-0]methyl 1H-indole-7-carboxylate</strong> (1.5 g) was added DMF (15 mL), and potassium tert-butoxide (1.5 g) was added thereto under ice-cooling, followed by stirring for 10 minutes. 4-(Bromomethyl)biphenyl (2.8 g) was added thereto, followed by stirring at room temperature for 19 hours. The reaction mixture was again ice-cooled, and a 10percent aqueous citric acid solution (20 mL) was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=97/3-95/5) to obtain methyl 1-(biphonyl-4-ylmethyl)-1H-indole-7-carboxylate (2.5 g).

References: [1]Patent: EP2277858,2011,A1 .Location in patent: Page/Page column 32-33.

53
[ 93247-78-0 ]
[ 1196052-12-6 ]

References: [1]Patent: EP2277858,2011,A1 .

54
[ 93247-78-0 ]
[ 1196046-87-3 ]

References: [1]Patent: EP2277858,2011,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

Related Functional Groups of
[ 93247-78-0 ]

Esters

A292273 [945655-38-9]

Ethyl 6-amino-2-phenyl-1H-indole-3-carboxylate

Similarity: 0.89

A379856 [312973-24-3]

Methyl 3-formyl-1H-indole-7-carboxylate

Similarity: 0.88

A161045 [205873-58-1]

Ethyl 1H-indole-7-carboxylate

Similarity: 0.88

A103557 [26000-33-9]

Methyl 9H-carbazole-2-carboxylate

Similarity: 0.88

A285956 [341988-36-1]

Methyl indoline-6-carboxylate

Similarity: 0.88

Related Parent Nucleus of
[ 93247-78-0 ]

Indoles

A292273 [945655-38-9]

Ethyl 6-amino-2-phenyl-1H-indole-3-carboxylate

Similarity: 0.89

A379856 [312973-24-3]

Methyl 3-formyl-1H-indole-7-carboxylate

Similarity: 0.88

A161045 [205873-58-1]

Ethyl 1H-indole-7-carboxylate

Similarity: 0.88

A114074 [1011-65-0]

Methyl 1H-indole-5-carboxylate

Similarity: 0.87

A238051 [50820-65-0]

Methyl 1H-indole-6-carboxylate

Similarity: 0.87

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 93247-78-0

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CAS No.: 93247-78-0

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{[proInfo.proName]}

CAS No.: 93247-78-0

{[proInfo.proName]}

CAS No.: 93247-78-0

Alternative Products

Product Details of [ 93247-78-0 ]

Safety of [ 93247-78-0 ]

Computational Chemistry of [ 93247-78-0 ] Show Less

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 93247-78-0 ]

[ 93247-78-0 ] Synthesis Path-Downstream 1~54

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 93247-78-0 ]

Esters

Related Parent Nucleus of [ 93247-78-0 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 93247-78-0 ]

Related Parent Nucleus of
[ 93247-78-0 ]