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

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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 1~41

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.

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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CAS No.: 93247-78-0

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