4771-48-6|4-Methyl-1H-indole-3-carbaldehyde| Ambeed

CAS No. :	4771-48-6
Formula :	C₁₀H₉NO
M.W :	159.19
SMILES Code :	CC1=CC=CC2=C1C(C=O)=CN2
MDL No. :	MFCD00049345
InChI Key :	OXMKZTMGJSTKPG-UHFFFAOYSA-N
Pubchem ID :	2762437

Safety of [ 4771-48-6 ]

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

Computational Chemistry of [ 4771-48-6 ] 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.	1.43
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	1.98

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)	1.22

Application In Synthesis of [ 4771-48-6 ]

* 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 [ 4771-48-6 ]

[ 4771-48-6 ] Synthesis Path-Downstream 1~55

1
[ 487-89-8 ]
Thallium tris(trifluoroacetate) [ No CAS ]
[ 59020-09-6 ]
[ 4771-48-6 ]
[ 108378-88-7 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1322 - 1326.

2
[ 594-27-4 ]
[ 141692-10-6 ]
[ 487-89-8 ]
[ 4771-48-6 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1322 - 1326.

3
[ 59020-09-6 ]
[ 141692-10-6 ]
[ 487-89-8 ]
[ 4771-48-6 ]
[ 108378-88-7 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1322 - 1326.

4
[ 141692-10-6 ]
[ 487-89-8 ]
[ 4771-48-6 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1322 - 1326.

6
[ 16096-32-5 ]
[ 68-12-2 ]
[ 4771-48-6 ]

Yield	Reaction Conditions	Operation in experiment
74%		General procedure: The Vilsmeier-Haack reagent was prepared by adding POCl3 (60 mmol, 6 mL) dropwise to ice-cold dry DMF (30 mL) whilst stirring. The mixture was then stirred for 10-15 min at 0 C. Compound 3b or 3e (10 mmol) was added as a solution in DMF (5 mL) to the above Vilsmeier-Haack reagent. The stirred mixture was then heated at 35 C for 1 h. After cooling, ice water (6 mL) and a 30% aqueous solution of NaOH (13 mL) were added successively, and the mixture was heated at reflux for 20 min and allowed to cool. The mixture was extracted with CH2Cl2 (20 mL*3). The extracts were dried over Na2SO4, evaporated under reduced pressure to remove the solvent, and the crude product was purified by flash column chromatography using 15-25% acetone/petroleum ether (60-90 C) as eluent to give the corresponding intermediate compound 4b or 4e, respectively.
	With trichlorophosphate; at 0 - 20℃;Inert atmosphere;	Procedure for Vilsmeiere-Haack reaction followed by LiAlH4 reduction was adapted from Petit et al.16 In a flame-dried flask under nitrogen, POCl3 (0.42 mL, 4.6 mmol) was added at 0 C to 4-methyl-1H-indole (0.5 g, 3.8 mmol) in DMF (7.6 mL). The reaction was stirred at room temperature overnight. 2 N NaOH(aq) was then added, the solution was stirred for 2 h, then poured into EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated. The crude aldehyde was carried forward without further purification.

References: [1]Chemical Biology and Drug Design,2011,vol. 78,p. 864 - 868.
[2]European Journal of Medicinal Chemistry,2015,vol. 92,p. 776 - 783.
[3]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1793 - 1798.
[5]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 3780 - 3790.
[6]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277.
[7]Angewandte Chemie - International Edition,2013,vol. 52,p. 3250 - 3254.
Angew. Chem.,2013,vol. 125,p. 3332 - 3336,5.
[8]Journal of Organic Chemistry,2013,vol. 78,p. 2362 - 2372.
[9]Tetrahedron,2013,vol. 69,p. 5622 - 5633.
[10]Chemistry - A European Journal,2015,vol. 21,p. 15104 - 15107.
[11]Chemistry - An Asian Journal,2015,vol. 10,p. 2738 - 2743.
[12]Organic Letters,2019,vol. 21,p. 2602 - 2605.
[13]Advanced synthesis and catalysis,2020.

7
[ 79-24-3 ]
[ 4771-48-6 ]
4-methyl-3-(2-nitro-propenyl)-1H-indole [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

8
[ 4771-48-6 ]
[ 75-52-5 ]
4-methyl-3-(2-nitro-vinyl)-1H-indole [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

9
[ 16096-32-5 ]
[ 3724-43-4 ]
[ 4771-48-6 ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

10
[ 4771-48-6 ]
[ 98-59-9 ]
[ 858101-82-3 ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277.
[3]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

11
[ 4771-48-6 ]
[ 74-88-4 ]
[ 170489-16-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1793 - 1798.
[2]Organic Letters,2019,vol. 21,p. 2602 - 2605.

12
[ 4771-48-6 ]
4-(1,4-dimethyl-1H-indol-3-ylmethylene)-5-(4-methyl-[1,2,3]thiadiazol-5-yl)-2,4-dihydro-pyrazol-3-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1793 - 1798.

13
[ 4771-48-6 ]
[ 858101-84-5 ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

14
[ 4771-48-6 ]
(-)-(1R,2R)-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

15
[ 4771-48-6 ]
cis-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

16
[ 4771-48-6 ]
cis-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

17
[ 4771-48-6 ]
(+)-(1S,2S)-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

18
[ 4771-48-6 ]
(+/-)-trans-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

19
[ 4771-48-6 ]
(+/-)-cis-ethyl 2-(4-methyl-1-tosyl-1H-indol-3-yl)cyclopropane-1-carboxylate [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2651 - 2654.

20
[ 4771-48-6 ]
[ 62500-89-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

21
[ 4771-48-6 ]
[ 3569-29-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

22
[ 4771-48-6 ]
1-(3-chloro-phenyl)-2-[2-(4-methyl-1H-indol-3-yl)-ethylamino]-ethanol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

23
[ 4771-48-6 ]
1-(3-chloro-phenyl)-2-[1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamino]-ethanol [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1301 - 1305.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 15 (E)-3-(4-Methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (Compound 15) Process 1 A mixture of N,N-dimethylformamide (6 ml) and phosphorus oxychloride (1.78 g) was stirred at room temperature for 30 minutes. 4-Methylindole (1.0 g) was added to the reaction solution, followed by stirring at room temperature for one hour. A 5N aqueous solution of sodium hydroxide (15 ml) was added thereto, followed by stirring at 100 C. for further 30 minutes. The reaction solution was cooled, and the precipitated crystals were collected by filtration to give 4-methylindole-3-carboxaldehyde (Compound III-1, 1.14 g). 1 H-NMR (90 MHz, CDCl3) delta2.83 (s, 3H), 6.98-7.29 (m, 3H), 7.89 (d, J=3.0 Hz, 1H), 9.11 (brs, 1H), 10.10 (s, 1H) EI-MS m/z=159 (M+)

25
[ 4771-48-6 ]
[ 22483-09-6 ]
C₁₄H₁₈N₂O₂ [ No CAS ]

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

26
[ 4771-48-6 ]
[ 98-09-9 ]
[ 1262322-58-6 ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure: NaH (60% 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]Journal of Medicinal Chemistry,2018,vol. 61,p. 7877 - 7891.

27
[ 123-75-1 ]
[ 4771-48-6 ]
C₁₄H₁₆N₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

28
[ 4771-48-6 ]
[ 1422432-75-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

29
[ 4771-48-6 ]
[ 1422432-95-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

30
[ 4771-48-6 ]
[ 1428648-21-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

31
[ 4771-48-6 ]
[ 1428648-64-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

32
[ 4771-48-6 ]
[ 1422433-24-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

33
[ 4771-48-6 ]
[ 1422432-61-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 944 - 948.

34
[ 4771-48-6 ]
[ 81784-47-6 ]

Yield	Reaction Conditions	Operation in experiment
43%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 8.5h;Reflux;	A solution of <strong>[4771-48-6]4-methyl-1H-indole-3-carbaldehyde</strong> (2.200 g, 13.82 mmol) in THF (50 mL) was added to a refluxing mixture of lithium aluminum hydride (1.154 g, 30.4 mmol) in THF (50 mL) (reflux condenser fitted to a two neck flask) over 30 min. The reaction mixture was refluxed for 8 hours, cooled to room temperature and treated with diethyl ether (~50 mL). The reaction mixture was acidified to ~pH 3 with 1N HCl, while cooling in an ice bath. The reaction mixture was diluted with EtOAc (125 mL), poured into a separatory funnel and washed with water (2X 50 mL), saturated aqueous NaCl solution (50 mL), then dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford 3,4-dimethyl-1H-indole (0.870 g, 5.99 mmol, 43% yield). LC retention time 1.15 min [Method F1]. MS (E-) m/z: 146.0 (M-H).
	With lithium aluminium tetrahydride; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux;	In a flame-dried flask under nitrogen, a solution of the Vilsmeiere-Haack product (0.39 g, 2.5 mmol) in THF (5 mL) was added dropwise to a suspension of LiAlH4 (0.19 g, 5 mmol) in THF (1.6 mL). The reaction was heated to reflux for 4 h, then cooled to room temperature and stirred overnight. The reaction was diluted with Et2O and cooled to 0 C. Water (0.19 mL) was added slowly, then 15% NaOH(aq) (0.19 mL), then water (0.6 mL) were added. The mixture was warmed to room temperature and stirred for 15 min. Some MgSO4 was added, the mixture was stirred for 15 min, filtered, and concentrated. The crude indole was carried forward without further purification.
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 8h;Cooling with ice; Green chemistry;	General procedure: This method is a general method. To a dry flask, LiAlH4 (15.0 mmol) was added, and TauHF (30.0 mL) was used as a solvent. The above-mentioned crude indole-3-formaldehyde THF (30.0 mL) solution was added dropwise under ice-water bath, and the mixture was allowed to react to room temperature for about 8 hours. The reaction was completely monitored by TLC. To the flask was added 1.0 mL of ice water, and then 1.5 g of NaOH solid and 3.0 mL of water were slowly added. After the reaction was completed, the mixture was stirred at room temperature for about 15 minutes, then the solid was filtered, and the filtrate was extracted with ethyl acetate. (3X 20.0 mL). After EtOAc (EtOAc/EtOAc/EtOAc. The desired 3-methylindoles and derivatives are obtained.

References: [1]Patent: WO2019/99336,2019,A1 .Location in patent: Page/Page column 180; 181.
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 3250 - 3254.
Angew. Chem.,2013,vol. 125,p. 3332 - 3336,5.
[3]Tetrahedron,2013,vol. 69,p. 5622 - 5633.
[4]Chemistry - A European Journal,2015,vol. 21,p. 15104 - 15107.
[5]Organic Letters,2017,vol. 19,p. 222 - 225.
[6]Patent: CN108101830,2018,A .Location in patent: Paragraph 0037; 0039; 0178.
[7]Advanced synthesis and catalysis,2020.

35
[ 4771-48-6 ]
[ 1428236-46-7 ]
C₂₁H₂₁NO₃ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 3250 - 3254.
Angew. Chem.,2013,vol. 125,p. 3332 - 3336,5.

36
[ 4771-48-6 ]
[ 1423754-11-3 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 2362 - 2372.

37
[ 4771-48-6 ]
[ 1423754-17-9 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 2362 - 2372.

38
[ 4771-48-6 ]
tosyl halogenide [ No CAS ]
[ 858101-82-3 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 2362 - 2372.

39
[ 4771-48-6 ]
[ 1441805-84-0 ]
C₁₇H₁₉F₃N₂O₃ [ No CAS ]

References: [1]Tetrahedron,2013,vol. 69,p. 5622 - 5633.

40
[ 4771-48-6 ]
[ 81784-49-8 ]

References: [1]Tetrahedron,2013,vol. 69,p. 5622 - 5633.
[2]Chemistry - A European Journal,2015,vol. 21,p. 15104 - 15107.
[3]Advanced synthesis and catalysis,2020.

41
[ 4771-48-6 ]
[ 1441806-55-8 ]
C₁₇H₂₁F₃N₂O₃ [ No CAS ]

References: [1]Tetrahedron,2013,vol. 69,p. 5622 - 5633.

42
[ 4771-48-6 ]
C₂₂H₂₁NO₅S [ No CAS ]
C₂₂H₂₁NO₅S [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

43
[ 4771-48-6 ]
C₁₈H₁₉NO₃S [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

44
[ 4771-48-6 ]
[ 1262322-65-5 ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

45
[ 4771-48-6 ]
C₂₂H₂₁NO₅S [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

46
[ 4771-48-6 ]
C₂₆H₂₉NO₆S [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

47
[ 4771-48-6 ]
C₂₄H₂₅NO₅S [ No CAS ]

References: [1]Journal of the American Chemical Society,2015,vol. 137,p. 3225 - 3228.

48
[ 4771-48-6 ]
5-(4-methyl-1H-indol-3-yl)oxazole [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 92,p. 776 - 783.

49
[ 4771-48-6 ]
4-chloro-5-(4-methyl-1H-indol-3-yl)oxazole [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2015,vol. 92,p. 776 - 783.

50
[ 4771-48-6 ]
dimethyl 4,8,8b-trimethyl-1-(p-tolyl)-3a,4-dihydro-1H-furo[3,4-b]indole-3,3(8bH)-dicarboxylate [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 15104 - 15107.

51
[ 4771-48-6 ]
[ 24424-99-5 ]
tert-butyl 3-formyl-4-methyl-1H-indole-1-carboxylate [ No CAS ]

References: [1]Chemistry - An Asian Journal,2015,vol. 10,p. 2738 - 2743.
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 6734 - 6750.

52
[ 16096-32-5 ]
[ 100-97-0 ]
[ 4771-48-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iodine; oxygen; pyrographite; In N,N-dimethyl-formamide; at 120℃; for 1.5h;	General procedure: A 50 mL round bottom flask equipped with a magnetic stirring bar was charged with substituted indole 1 (1.0 mmol, 1.0 equiv), HMTA (2.0 mmol, 0.2803 g, 2.0 equiv), activated carbon (0.1 g) and DMF (2 mL). Then I2 (0.2 mmol, 0.0507g, 20 mol%) was added and the flask was equipped with a reflux condenser. The reaction mixture was stirred at 120 oC under open air and monitored by TLC. Upon completion of the reaction, the reaction mixture was cooled to room temperature. The resultant mixture was filtered through a pad of celite and the filter cake was washed thoroughly with EtOAc (4 × 6 mL). The filtrate was washed with 0.5 M aqueous HCl (10 mL), saturated NaHCO3 solution (10 mL) and saturated NaCl solution ( 10 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluted with hexane and ethyl acetate to give the product.
78%	With aluminum (III) chloride; In N,N-dimethyl-formamide; at 120℃; for 2.4h;	General procedure: A method for synthesizing compound III-1 wherein R1, R2 and R3 are simultaneously hydrogen in the formula III, the method comprising the steps of:(1) Add to a 50 mL round bottom flask1.0mmol indole(In the formula I, R1, R2, and R3 are both hydrogen) and1.0 mmol (0.140 g) of hexamethylenetetramine, then 2 mL of N,N-dimethylformamide (DMF), stirred in a magnetic stirrer to dissolve the solid, followed by the addition of 0.05 mmol (0.012 g) of crystalline trichloride Aluminum, connected to a reflux condenser, heated at 120 C, the reaction progress was monitored by TLC, and the reaction was cooled to room temperature after 1 h to prepare a suspension;(2) The suspension prepared in the step (1) is suction filtered with a funnel padded with diatomaceous earth.The filter cake was washed well with ethyl acetate, suction filtered, and the above operation was repeated until the filtrate had no product, and all the filtrates were combined.Dilute with 15 mL of saturated saline solution, disperse and separate the layers, and the aqueous layer was further extracted with ethyl acetate three times.Each time 10 mL, the ethyl acetate layer was combined and washed with 10 mL of 2 mol/L diluted hydrochloric acid.Wash with 10 mL of saturated sodium bicarbonate solution, and finally wash with 10 mL of saturated brine.The washed ethyl acetate layer was dried over anhydrous sodium sulfate, and after drying, the desiccant was filtered off.Then use a rotary evaporator to recover the solvent to concentrate the product, and finally,The residue is subjected to silica gel column chromatography using a mixture of n-hexane-ethyl acetate (V/V = 2:1) as an eluent to obtain a purified product.The mass of the compound III-indole-3-carbaldehyde is 0.137g,The product yield was 94%.

References: [1]Tetrahedron Letters,2017,vol. 58,p. 2877 - 2880.
[2]Patent: CN108329249,2018,A .Location in patent: Paragraph 0041-0044; 0051-0054.

53
[ 4771-48-6 ]
[ 2769-64-4 ]
[ 433733-19-8 ]
C₂₈H₃₂N₂O₃ [ No CAS ]

References: [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 4507 - 4510.

54
[ 4771-48-6 ]
C₂₅H₂₇N₃O [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 222 - 225.

55
[ 4771-48-6 ]
C₂₅H₂₇N₃O [ No CAS ]

References: [1]Organic Letters,2017,vol. 19,p. 222 - 225.

Historical Records

Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 4771-48-6 ]

Aldehydes

A134188 [4771-49-7]

6-Methyl-1H-indole-3-carbaldehyde

Similarity: 0.98

A140574 [52562-50-2]

5-Methyl-1H-indole-3-carbaldehyde

Similarity: 0.98

A162961 [487-89-8]

Indole-3-carboxaldehyde

Similarity: 0.98

A185448 [141835-34-9]

5-Phenyl-1H-indole-3-carbaldehyde

Similarity: 0.98

A248249 [5416-80-8]

2-Methyl-1H-indole-3-carbaldehyde

Similarity: 0.94

Related Parent Nucleus of
[ 4771-48-6 ]

Indoles

A134188 [4771-49-7]

6-Methyl-1H-indole-3-carbaldehyde

Similarity: 0.98

A140574 [52562-50-2]

5-Methyl-1H-indole-3-carbaldehyde

Similarity: 0.98

A162961 [487-89-8]

Indole-3-carboxaldehyde

Similarity: 0.98

A185448 [141835-34-9]

5-Phenyl-1H-indole-3-carbaldehyde

Similarity: 0.98

A172588 [703-80-0]

3-Acetylindole

Similarity: 0.94

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CAS No.: 4771-48-6

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