4771-49-7|6-Methyl-1H-indole-3-carbaldehyde| Ambeed

Structure of 4771-49-7

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Quality Control of [ 4771-49-7 ] Purity: 98% SDS Specification

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Product Details of [ 4771-49-7 ]

CAS No. :	4771-49-7
Formula :	C₁₀H₉NO
M.W :	159.18
SMILES Code :	O=CC1=CNC2=C1C=CC(C)=C2
MDL No. :	MFCD00049347
InChI Key :	LZERQSJGPXFAKB-UHFFFAOYSA-N
Pubchem ID :	4777902

Safety of [ 4771-49-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 4771-49-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
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	48.65
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.	1.46
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	1.88
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.29
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.	1.18
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	3.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.99

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.5
Solubility	0.503 mg/ml ; 0.00316 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.	-2.19
Solubility	1.02 mg/ml ; 0.00642 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	-3.61
Solubility	0.0393 mg/ml ; 0.000247 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.94 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	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.18

Application In Synthesis of [ 4771-49-7 ]

* 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 [ 4771-49-7 ]

[ 4771-49-7 ] Synthesis Path-Downstream 1~35

1
[ 123-75-1 ]
[ 4771-49-7 ]
[ 75629-47-9 ]

References: [1]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 1711 - 1721.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

2
[ 79-24-3 ]
[ 4771-49-7 ]
[ 566200-36-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 315 - 319.

3
[ 4771-49-7 ]
[ 940304-80-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 22℃; for 3h;	10.1. To a solution of <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> (0.96 g, Lit. 5) in ethanol (30 ml) was added at 22° C. hydroxylamine hydrochloride (0.46 g) and sodium acetate (0.54 g) and the mixture was stirred for 3 h. The mixture was evaporated and the residue triturated with water and dichloromethane/n-heptane (1:1) and dried to give <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> oxime (0.96 g) as a pink solid. MS: 175.3 ([M+H]+).

References: [1]Patent: US2008/96953,2008,A1 .Location in patent: Page/Page column 11.

4
[ 4771-49-7 ]
2,4,6-trimethyl-N-[1-methyl-2-(6-methyl-1H-indol-3-yl)ethyl]benzenesulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 315 - 319.

5
[ 4771-49-7 ]
[ 4771-76-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 315 - 319.
[2]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 184 - 198.
[3]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

6
[ 4771-49-7 ]
1-(3-chloro-phenyl)-2-[1-methyl-2-(6-methyl-1<i>H</i>-indol-3-yl)-ethylamino]-ethanol [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 184 - 198.
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

7
sodium metabisulfite [ No CAS ]
[ 4771-49-7 ]
thallium(III) trifluoroacetate [ No CAS ]
[ 338760-54-6 ]

Yield	Reaction Conditions	Operation in experiment
283 mg (79%)	With potassium iodide; In diethyl ether; water; trifluoroacetic acid;	(a) Preparation of 6-methyl-4-iodo-indole-3-carboxaldehyde A solution of thallium (III) trifluoroacetate (1 g 1.84 mmol) in trifluoroacetic acid (15 mL) was added to 6-methyl-indole-3-carboxaldehyde (200 mg, 1.25 mmol) and the resulting mixture was stirred at 30° C. for 2 h. The solvent was removed under vacuum (rotary evaporator). To the residue was added an aqueous solution of potassium iodide (2 g, 12 mmol, in 20 mL of water) and the mixture was stirred at room temperature overnight. Solid sodium meta-bisulfite was added to the reaction mixture until it turned yellow. The mixture was basified with aqueous NaOH solution and was extracted repeatedly from diethyl ether. The combined organic was washed with brine and was dried over magnesium sulfate. Evaporation of solvent gave the crude product, which was purified by flash chromatography by using EtOAc as eluent. The product, 6-methyl-4-iodo-indole-3-carboxaldehyde was isolated as solid to yield 283 mg (79percent) of the desired product. MS: 286.

References: [1]Patent: US6455525,2002,B1 .

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 32 (E)-3-(6-Methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 32) Process 1 Substantially the same procedure as in Process 1 of Example 15 was repeated using 6-methylindole (1.15 g) to give 6-methylindole-3-carboxaldehyde (1.34 g). 1H-NMR (270 MHz, CDCl3) delta2.47 (s, 3H), 7.10 (d, J=8.0 Hz, 1H), 7.24 (brs, 1H), 7.75 (d, J=2.6 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H), 9.99 (s, 1H), 10.55 (brs, 1H) EI-MS m/z=159 (M+)

9
[ 110-89-4 ]
[ 191671-30-4 ]
[ 108-20-3 ]
[ 4771-49-7 ]
[ 191670-92-5 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 106 (Z)-2-(beta-D-Glucosylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 106) 2-(beta-D-Glucosylthio)-3',4',5'-trimethoxy-acetophenone (1.01 g) obtained in Reference Example 17 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.40 g) were dissolved in ethanol (10 ml), and piperidine (0.21 g) was added thereto, followed by heating under reflux for 24 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethanol and purified by preparative HPLC (YMC pack ODS, SH-343-5, S-5, 120A, 250*20 mm, acetonitrile:water=40:60). The elude was concentrated under reduced pressure and the residue was recrystallized from a mixed solvent of ethanol and isopropyl ether (1:1) to give Compound 106 (322.2 mg). 1 H-NMR (270 MHz, DMSO-d6) delta2.40 (s, 3H), 2.78 (m, 1H), 3.16-3.32 (m, 5H), 3.79 (s, 3H), 3.80 (s, 3H), 3.81 (s, 3H), 4.24 (t, J=5.6 Hz, 1H), 4.76 (d, J=8.6 Hz, 1H), 4.82 (d, J=4.6 Hz, 1H), 5.09 (d, J=2.9 Hz, 1H), 5.46 (d, J=5.0 Hz, 1H), 6.94 (d, J=8.3 Hz, 1H), 7.09 (s, 2H), 7.26 (s, 1H), 7.33 (d, J=8.3 Hz, 1H), 7.52 (s, 1H), 8.12 (d, J=2.5 Hz, 1H), 11.73 (s, 1H) FAB-MS m/z=545 (M+ +1) Elemental Analysis: C27 H31 NO9 S.0.8H2 O Calcd.(percent): C, 57.91; H, 5.87; N, 2.50 Found (percent): C, 57.88; H, 5.77; N, 2.40
	In ethanol;	Example 14 (Z)-2-(beta-D-Glucosylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 14) 2-(beta-D-Glucosylthio)-3',4',5'-trimethoxyacetophenone (1.01 g) obtained in Reference Example 17 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.40 g) were dissolved in ethanol (10 ml), and piperidine (0.21 g) was added thereto, followed by heating under reflux for 24 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethanol and purified by preparative HPLC (YMC pack ODS, SH-343-5, S-5, 120A, 250 x 20 mm, acetonitrile:water = 40:60). The elude was concentrated under reduced pressure and the residue was recrystallized from a mixed solvent of ethanol and isopropyl ether (1:1) to give Compound 14 (322.2 mg). 1H-NMR (270 MHz, DMSO-d6) delta 2.40 (s, 3H), 2.78 (m, 1H), 3.16-3.32 (m, 5H), 3.79 (s, 3H), 3.80 (s, 3H), 3.81 (s, 3H), 4.24 (t, J = 5.6 Hz, 1H), 4.76 (d, J = 8.6 Hz, 1H), 4.82 (d, J = 4.6 Hz, 1H), 5.09 (d, J = 2.9 Hz, 1H), 5.46 (d, J = 5.0 Hz, 1H), 6.94 (d, J = 8.3 Hz, 1H), 7.09 (s, 2H), 7.26 (s, 1H), 7.33 (d, J = 8.3 Hz, 1H), 7.52 (s, 1H), 8.12 (d, J = 2.5 Hz, 1H), 11.73 (s, 1H) FAB-MS m/z = 545 (M++1)

References: [1]Patent: US5952355,1999,A .
[2]Patent: EP812825,1997,A1 .

10
[ 110-89-4 ]
[ 191671-29-1 ]
[ 4771-49-7 ]
(Z)-2-(2,3-dihydroxypropylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; hexane; ethyl acetate;	EXAMPLE 120 (Z)-2-(2,3-Dihydroxypropylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 120) 2-(2,3-Dihydroxypropylthio)-3',4',5'-trimethoxy-acetophenone (1.58 g) obtained in Reference Example 16 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (975.0 mg) were dissolved in ethanol (10 ml), and piperidine (494.5 mg) was added thereto, followed by heating under reflux for 36 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) to give Compound 120 (1.23 g). 1 H-NMR (270 MHz, CDCl3) delta2.36 (s, 1H), 2.46 (s, 3H), 2.82 (dd, J=13.9, 8.9 Hz, 1H), 3.08 (dd, J=13.9, 4.0 Hz, 1H), 3.55 (m, 1H), 3.68 (m, 1H), 3.77 (m, 1H), 3.87 (s, 6H), 3.97 (s, 3H), 4.16 (s, 1H), 7.04 (d, J=7.7 Hz, 1H), 7.10 (s, 2H), 7.24 (s, 1H), 7.41 (d, J=7.7 Hz, 1H), 7.96 (s, 1H), 8.54 (d, J=3.0 Hz, 1H), 8.96 (s, 1H) EI-MS m/z=457 (M+) Elemental Analysis: C24 H27 NO6 S.0.2H2 O Calcd.(percent): C, 62.51; H, 5.99; N, 3.04 Found (percent): C, 62.46; H, 6.11; N, 2.95
	In ethanol; hexane; ethyl acetate;	Example 28 (Z)-2-(2,3-Dihydroxypropylthio)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 28) 2-(2,3-Dihydroxypropylthio)-3',4',5'-trimethoxyacetophenone (1.58 g) obtained in Reference Example 16 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (975.0 mg) were dissolved in ethanol (10 ml), and piperidine (494.5 mg) was added thereto, followed by heating under reflux for 36 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) to give Compound 28 (1.23 g). 1H-NMR (270 MHz, CDCl3) delta 2.36 (s, 1H), 2.46 (s, 3H), 2.82 (dd, J = 13.9, 8.9 Hz, 1H), 3.08 (dd, J = 13.9, 4.0 Hz, 1H), 3.55 (m, 1H), 3.68 (m, 1H), 3.77 (m, 1H), 3.87 (s, 6H), 3.97 (s, 3H), 4.16 (s, 1H), 7.04 (d, J = 7.7 Hz, 1H), 7.10 (s, 2H), 7.24 (s, 1H), 7.41 (d, J = 7.7 Hz, 1H), 7.96 (s, 1H), 8.54 (d, J = 3.0 Hz, 1H), 8.96 (s, 1H) EI-MS m/z = 457 (M+)

References: [1]Patent: US5952355,1999,A .
[2]Patent: EP812825,1997,A1 .

11
[ 110-89-4 ]
[ 191671-34-8 ]
[ 4771-49-7 ]
[ 191670-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; hexane; water; ethyl acetate;	EXAMPLE 112 (E)-2-(3,4-Dihydroxybutyl)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 112) 5,6-Dihydroxy-1-(3,4,5-trimethoxyphenyl)hexan-1-one (870.0 mg) obtained in Reference Example 21 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (465.0 mg) were dissolved in ethanol (8 ml), and piperidine (288.8 mg) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) and then from a mixed solvent of ethanol and water (1:1) to give Compound 112 (142.7 mg). 1 H-NMR (270 MHz, CDCl3) delta1.70-1.95 (m, 2H), 2.36 (brs, 1H), 2.47 (s, 3H), 2.87 (m, 1H), 3.03 (m, 1H), 3.54 (m, 1H), 3.65 (m, 1H), 3.77 (m, 1H), 3.88 (s, 6H), 3.96 (s, 3H), 4.04 (brs, 1H), 7.00 (s, 2H), 7.02 (d, J=8.8 Hz, 1H), 7.22 (s, 1H), 7.41 (d, J=8.8 Hz, 1H), 7.75 (s, 1H), 7.79 (d, J=2.3 Hz, 1H), 8.79 (s, 1H) FAB-MS m/z=440 (M+ +1) Elemental Analysis: C25 H29 NO6.0.3H2 O Calcd.(percent): C, 67.49; H, 6.71; N, 3.15 Found (percent): C, 67.55; H, 6.93; N, 3.15
	In ethanol; hexane; water; ethyl acetate;	Example 20 (E)-2-(3,4-Dihydroxybutyl)-3-(6-methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 20) 5,6-Dihydroxy-1-(3,4,5-trimethoxyphenyl)hexan-1-one (870.0 mg) obtained in Reference Example 21 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (465.0 mg) were dissolved in ethanol (8 ml), and piperidine (288.8 mg) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane (5:3) and then from a mixed solvent of ethanol and water (1:1) to give Compound 20 (142.7 mg). 1H-NMR (270 MHz, CDCl3) delta 1.70-1.95 (m, 2H), 2.36 (brs, 1H), 2.47 (s, 3H), 2.87 (m, 1H), 3.03 (m, 1H), 3.54 (m, 1H), 3.65 (m, 1H), 3.77 (m, 1H), 3.88 (s, 6H), 3.96 (s, 3H), 4.04 (brs, 1H), 7.00 (s, 2H), 7.02 (d, J = 8.8 Hz, 1H), 7.22 (s, 1H), 7.41 (d, J = 8.8 Hz, 1H), 7.75 (s, 1H), 7.79 (d, J = 2.3 Hz, 1H), 8.79 (s, 1H) FAB-MS m/z = 440 (M++1)

References: [1]Patent: US5952355,1999,A .
[2]Patent: EP812825,1997,A1 .

12
[ 110-89-4 ]
[ 191671-38-2 ]
[ 4771-49-7 ]
[ 243636-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 128 3-(6-Methylindol-3-yl)-2-[(2S),(3R)-2,3,4-trihydroxy-butylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 128) 3',4',5'-Trimethoxy-2-[(2S),(3R)-2,3,4-trihydroxy-butylthio]acetophenone (1.73 g) obtained in Reference Example 22 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 26 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 128 (1.22 g). 1 H-NMR (270 MHz, CDCl3) delta2.43 (s, 3H), 2.96 (dd, J=13.6, 8.7 Hz, 1H), 3.10 (dd, J=13.6, 4.0 Hz, 1H), 3.23 (brs, 1H), 3.53-3.82 (m, 5H), 3.84 (s, 6H), 3.96 (s, 3H), 4.84 (brs, 1H), 7.00 (d, J=8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J=2.6 Hz, 1H), 9.39 (brs, 1H) FAB-MS m/z=488 (M+ +1) Elemental Analysis: C25 H29 NO7 S Calcd.(percent): C, 61.59; H, 6.00; N, 2.87 Found (percent): C, 61.26; H, 6.12; N, 2.82
	In ethanol;	Example 36 3-(6-Methylindol-3-yl)-2-[(2S),(3R)-2,3,4-trihydroxybutylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 36) 3',4',5'-Trimethoxy-2-[(2S),(3R)-2,3,4-trihydroxybutylthio]acetophenone (1.73 g) obtained in Reference Example 22 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 26 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 36 (1.22 g). 1H-NMR (270 MHz, CDCl3) delta 2.43 (s, 3H), 2.96 (dd, J = 13.6, 8.7 Hz, 1H), 3.10 (dd, J = 13.6, 4.0 Hz, 1H), 3.23 (brs, 1H), 3.53-3.82 (m, 5H), 3.84 (s, 6H), 3.96 (s, 3H), 4.84 (brs, 1H), 7.00 (d, J = 8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.36 (d, J = 8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J = 2.6 Hz, 1H), 9.39 (brs, 1H) FAB-MS m/z = 488 (M++1)

References: [1]Patent: US5952355,1999,A .
[2]Patent: EP812825,1997,A1 .

13
[ 110-89-4 ]
[ 191671-42-8 ]
[ 4771-49-7 ]
[ 243636-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	EXAMPLE 129 3-(6-Methylindol-3-yl)-2-[(2R),(3S)-2,3,4-trihydroxy-butylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 129) 3',4',5'-Trimethoxy-2-[(2R),(3S)-2,3,4-trihydroxy-butylthio]acetophenone (1.73 g) obtained in Reference Example 23 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 129 (1.12 g). 1 H-NMR (270 MHz, CDCl3) delta2.43 (s, 3H), 2.95 (dd, J=13.6, 8.7 Hz, 1H), 3.10 (dd, J=13.6, 4.0 Hz, 1H), 3.17 (brs, 1H), 3.53 (d, J=6.3 Hz, 1H), 3.64-3.82 (m, 4H), 3.84 (s, 6H), 3.96 (s, 3H), 4.83 (d, J=4.0 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.37 (d, J=8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J 2.6 Hz, 1H), 9.36 (brs, 1H) FAB-MS m/z=488 (M+ +1) Elemental Analysis: C25 H29 NO7 S Calcd.(percent): C, 61.59; H, 6.00; N, 2.87 Found (percent): C, 61.56; H, 6.14; N, 2.82
	In ethanol;	Example 37 3-(6-Methylindol-3-yl)-2-[(2R),(3S)-2,3,4-trihydroxybutylthio]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 37) 3',4',5'-Trimethoxy-2-[(2R),(3S)-2,3,4-trihydroxybutylthio]acetophenone (1.73 g) obtained in Reference Example 23 and <strong>[4771-49-7]6-methylindole-3-carbaldehyde</strong> (0.80 g) were dissolved in ethanol (10 ml), and piperidine (0.43g) was added thereto, followed by heating under reflux for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 37 (1.12 g). 1H-NMR (270 MHz, CDCl3) delta 2.43 (s, 3H), 2.95 (dd, J = 13.6, 8.7 Hz, 1H), 3.10 (dd, J = 13.6, 4.0 Hz, 1H), 3.17 (brs, 1H), 3.53 (d, J = 6.3 Hz, 1H), 3.64-3.82 (m, 4H), 3.84 (s, 6H), 3.96 (s, 3H), 4.83 (d, J = 4.0 Hz, 1H), 7.01 (d, J = 8.2 Hz, 1H), 7.07 (s, 2H), 7.20 (s, 1H), 7.37 (d, J = 8.2 Hz, 1H), 7.97 (s, 1H), 8.59 (d, J = 2.6 Hz, 1H), 9.36 (brs, 1H) FAB-MS m/z = 488 (M++1)

References: [1]Patent: US5952355,1999,A .
[2]Patent: EP812825,1997,A1 .

14
CH₃ I [ No CAS ]
[ 4771-49-7 ]
1,6-dimethyl-1H-indole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With NaH; In N,N-dimethyl-formamide;	EXAMPLE 1 3-(1,6-dimethyl-1H-indol-3-yl)-4-(1-methyl-1H-indol-3yl)-pyrrole-2,5-dione A solution of the known <strong>[4771-49-7]6-methyl-1H-indole-3-carboxaldehyde</strong> (5 g, 31 mm) in DMF (100 mL) was cooled to 0° C. and treated with NaH (38 mm), and stirred at 0° C. for 3 hours. After treatment with CH3 I (2.35 mL, 38 mm), the mixture was allowed to warm to room temperature overnight. The mixture was poured into H2 O(500 mL) and extracted with ethylacetate (EtOAc) (200 mL*3). The combined organic layers were dried over MgSO4, filtered and evaporated. Purification by flash column chromatography afforded 1,6-dimethyl-1H-indole-3-carboxaldehyde (5.2 g, 97percent).

References: [1]Patent: US5891901,1999,A .

15
[ 110-89-4 ]
[ 4771-49-7 ]
[ 34293-23-7 ]
(3E)-5-(6-methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water;	EXAMPLE 1 Preparation of (3E)-5-(6-Methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone A mixture of 4.77 g. of <strong>[4771-49-7]6-methylindole-3-carboxaldehyde</strong>, 4.24 g. of dimethylcreatinine, and 50 ml. of piperidine was heated at reflux for 24 hours. The cooled suspension was poured into 250 ml. of water, and the yellow precipitate was collected by filtration, washed with water and dried in vacuo and afforded 7.0 g. of crude 5-(6-methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone. Recrystallization from acetonitrile gave 4.50 g. of (3E)-5-(6-methylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinone, melting point 227°-228°. Calcd. for C16 H18 N4 O: C, 68.07; H, 6.43; N, 19.84. Found: C, 67.86; H, 6.38; N, 19.68. Mass spectrum, m/e 282; UV (95percent ethanol): 233 nm.(epsilon23,600); 275 nm (8300), 392 nm (23,400); NMR (100 mHz, DMSO-d6): delta 8.61 (s, 1H, H-2), 6.36 (broad, 1H, --CH=C--CO).

References: [1]Patent: US4176230,1979,A .

16
[ 54681-67-3 ]
[ 4771-49-7 ]
[ 71359-92-7 ]

Yield	Reaction Conditions	Operation in experiment
159.5 g (89%)	With pyridine; acetic anhydride;	EXAMPLE 31 Alpha-acetamido-6-methylindole-3-acrylic acid ethylester A 3-l. three-necked flask, equipped with a mechanical stirrer, a thermometer and a dropping funnel with pressure-equalizing arm was charged with 100 g (0.63 mol) of <strong>[4771-49-7]6-methylindole-3-carboxaldehyde</strong>, 119 g (0.63 mol) of acetamidomalonic acid monoethylester and 500 ml of pyridine. The mixture was stirred and kept at 15° with a cold water bath while 175 ml of acetic anhydride was added over 15 minutes. The yellow solution was stirred at room temperature for 3 hours. Then an additional portion of 36 g (0.19 mol) of acetamidomalonic acid monoethyl ester was added and stirring at room temperature was continued for 22 hours before 1 kg of ice was added. The temperature fell to -10° and the product began to precipitate. The suspension was stirred at room temperature for 5 hours and poured into 2 1 of water. After 20 minutes, the precipitate was collected by suction filtration, washed with water and dried at 50° in an air oven overnight to afford 159.5 g (89percent) of crude product as yellow crystals, m.p. 159°-162° (sinters at 75°).

References: [1]Patent: US4073795,1978,A .

17
[ 4771-49-7 ]
6-methyl-1H-indole-3-carbaldehyde oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 22℃; for 3h;	63.1. 6-Methyl-1H-indole-3-carbaldehyde oxime To a solution of <strong>[4771-49-7]6-methyl-1H-indole-3-carbaldehyde</strong> (0.96 g, Lit. 20) in ethanol (30 ml) was added at 22° C. hydroxylamine hydrochloride (0.46 g) and sodium acetate (0.54 g) and the mixture was stirred for 3 h. The mixture was evaporated and the residue triturated with water and dichloromethane/n-heptane (1:1) and dried to give the title compound (0.96 g) as a pink solid. MS: 175.3 ([M+H]+).

References: [1]Patent: US2007/129421,2007,A1 .Location in patent: Page/Page column 23.

18
[ 4771-49-7 ]
[ 194490-23-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With formic acid; hydroxylamine hydrochloride; sodium formate; for 1h;Heating / reflux;	Example 4; 1. Synthesis of indole derivatives; 1) Synthesis of 3-cyanoindole derivatives; [Show Image] Nine objective compounds were prepared by (1) formylation of 3-position of the corresponding indole using phosphorus oxychloride in the presence of dimethylformamide (Vilsmeier method), (2) cyanation by dehydrating reaction with hydroxylamine in sodium formate and formic acid, (3) coupling with ethyl 4-fluorobenzoate in the presence of potassium fluoride on almina and 18-crown-6-ether in dimethyl sulfoxide and then, (4) hydrolysis with lithium hydroxide in total 4 steps in that order (the following Table 2). In addition, XO-CH172 and XO-CH183 (R is a 2-methyl group or a 5-methoxy group, respectively) were prepared from the step (2) using the corresponding aldehydes purchased.; XO-CH186; XO-CH180 (1.14g, 7.16 mmol) was dissolved in formic acid (11 mL), to the solution were added hydroxylamine hydrochloride (0.63 g, 9.1 mmol) and sodium formate (0.90 g, 13 mmol). The mixture was heated for reflux for an hour. To the reaction mixture was added water under ice-cooling, and the mixture was stirred for a while. The solid was collected by filtration and dried 60°C under reduced pressure to give XO-CH186 as a red-black solid (0.85 g, 76percent yield).

References: [1]Patent: EP1932833,2008,A1 .Location in patent: Page/Page column 15; 19.

19
[ 4771-49-7 ]
[ 22483-09-6 ]
C₁₄H₁₈N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3780 - 3790.

20
[ 4771-49-7 ]
[ 98-09-9 ]
[ 1262322-60-0 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: NaH (60percent dispersion in mineral oil, 20.00 mmol, 0.48 g) wasa dded portionwise to a stirred solution of the aldehyde 4 (10.00 mmol) in anhydrous THF (25 mL) cooled in an ice bath. The resulting mixture was then slowly allowed to warm to r.t. After stirring for 30 min, PhSO2Cl (12.00 mmol) (CH3COCl 12.00 mmol for5f) in anhydrous THF (5 mL) was added dropwise. When TLC monitoring showed that the starting material 4 had disappeared, the reaction mixture was evaporated under reduced pressure to remove the solvent and was then diluted with ice water (50 mL). Solid products were filtered off and recrystallized from acetone/petroleum ether (60-90 °C) to give the desired intermediate 5.

References: [1]European Journal of Medicinal Chemistry,2015,vol. 92,p. 776 - 783.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277.
[3]Organic Letters,2013,vol. 15,p. 3910 - 3913.

21
[ 4771-49-7 ]
[ 98-59-9 ]
[ 1262322-61-1 ]

Yield	Reaction Conditions	Operation in experiment
79.82%	With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 - 5℃; for 2h;	Add III-3 (1.00g, 6.29mmol), DMAP (154mg, 1.26mmol), DIEA (3.16mL, 18.87mmol) to 100mL three-necked flask, stir and dissolve with 10mL acetonitrile, slowly add at 05C A solution of p-toluenesulfonyl chloride (IV-3, 1.44 g, 7.56 mmol) in 10 mL of acetonitrile was added, and stirring was continued for 2 h under low temperature conditions.TLC monitoring of raw material reactionsCompletely, concentrate the reaction solution, dissolve it with 30 mL of ethyl acetate, wash with 40 mL of water, and extract twice with ethyl acetate (20 mL×2)The organic phase is washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate; filtered, filtered, and then filtered and evaporated.After drying, 1.57gBeige solid V-7,The yield was 79.82%.

References: [1]Patent: CN109942545,2019,A .Location in patent: Paragraph 0125; 0127-0129.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277.
[3]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 5696 - 5705.

22
[ 6419-36-9 ]
[ 4771-49-7 ]
[ 1316694-93-5 ]