114144-17-1|5-Iodo-1H-indole-3-carbaldehyde| Ambeed

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Quality Control of [ 114144-17-1 ] Purity: 97% SDS Specification

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Product Details of [ 114144-17-1 ]

CAS No. :	114144-17-1
Formula :	C₉H₆INO
M.W :	271.05
SMILES Code :	O=CC1=CNC2=C1C=C(I)C=C2
MDL No. :	MFCD15176154
InChI Key :	UTEGGIRVAHNXDS-UHFFFAOYSA-N
Pubchem ID :	13863906

Safety of [ 114144-17-1 ]

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

Computational Chemistry of [ 114144-17-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	56.4
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.	1.58
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.58
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.74
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.62
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.34

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.37
Solubility	0.116 mg/ml ; 0.000426 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.	-2.48
Solubility	0.892 mg/ml ; 0.00329 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.18
Solubility	0.0178 mg/ml ; 0.0000658 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.42 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	0.0
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	2.0 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<0.0
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)	1.66

Application In Synthesis of [ 114144-17-1 ]

* 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 [ 114144-17-1 ]

[ 114144-17-1 ] Synthesis Path-Downstream 1~31

1
[ 16066-91-4 ]
[ 33513-42-7 ]
[ 114144-17-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With trichlorophosphate; at 0 - 40℃; for 1.5h;	General procedure: Phosphorus oxychloride (0.42 g, 2.74 mmol) was added dropwise to a solution of the indole 5b, 5e-5g (0.30 g, 2.29 mmol) in DMF (0.84 g, 11.4 mmol) at 0 C for 30 min. The solution was then heated at 40 C for 1 h. Ice was added to the reaction vessel, followed by a solution of sodium hydroxide (2 M). The solution was refluxed for 40 min. The mixture was cooled and extracted using ethyl acetate, and the organic phase was washed with brine. The organic extracts were combined, dried over Na2SO4, and concentrated. The crude residue was purified by chromatography on a silica gel column using hexane-ethyl acetate as an eluent to obtain the desired product [19].
77%		General procedure: Into a 25 mL tube, Ph3P (0.75 mmol, 1.5 equiv.), ICH2CH2I (0.75 mmol, 1.5 equiv.)indoles 1 (0.5 mmol, 1 equiv.), DMAP (0.5 mmol, 1 equiv.), and DMF (2 mL) wereadded under air atmosphere. The resulting mixture was stirred at 80 oC for 2 hours. H2O(5 mL) was added and stirred at 80 oC for another 2 hours. The mixture was cooled toroom temperature. A saturated aqueous brine solution was added, and the crude organicproduct was extracted by CH2Cl2. The combined organic phase was dried withanhydrous Na2SO4. After filtration, the solution was concentrated under reducedpressure to remove the solvent. The residue was subjected to flash columnchromatography on silica gel (pentane/ethyl acetate) to give the pure pro ducts 4j-4u.
48.27%		The starting reagent, 5-iodoindole-3-carboxaldehyde was prepared. Dimethylformamide (0.3602 g, 4.93 mmol) was reacted with phosphorus oxychloride (0.1908 g, 1.24 mmol) at 0 C. for 30 mm to produce an electrophilic iminium cation. After that 5-iodoin- dole (0.2978 g, 1.23 mmol) in DMF was added dropwise and stirred in an ice bath for 3 h. The reaction mixture was poured into ice-water, neutralized with iN NaOH, and lefi it overnight. Then, it was extracted with CH2C12, dried with MgSO4 anhydrous, and concentrated in vacuo before purification (50% EtOAc in hexane) to obtain orange solid (48.27%). Afier that the terminal alkyne product was prepared with the method described above and purified by column chromatography (20% EtOAc in hexane to EtOAc) to yield brown solid compound (38.21% over all steps). ‘H-NMR (400 MHz, CD3OD) ö 9.89 (s, 1H), 8.29 (s, 1H), 8.14 (s, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.36 (d, J=8.5 Hz, 1H),3.38 (s, 1H).

		General procedure: Phosphorous oxychloride (2 mmol) was added dropwise to dimethylformamide (3 mL) cooled under ice-bath and allowed to stir for 30 min. A solution of indoles 4a-4h or azaindole 5 (1 mmol) in DMF (5 mL) was added dropwise for 5 min at 0 oC. The mixture was further allowed to stir for 3 h at 90-100 oC. Reaction mixture was cooled to room temperature and poured into crushed ice. Excess POCl3 was quenched with 1 N NaOH and left overnight at room temperature. Ice-cold reaction mixture was then extracted (50 mL × 3) with EtOAc. Combined organic layer was concentrated on rotary evaporator and crude products were purified by silica gel (No.100-200) column chromatography to get indole-3-carboxaldehydes 1a-1h or 6 in 60-80% yield.
		General procedure: Phosphorus oxychloride (0.86 mL) was added dropwise to dimethylformamide (1.0 mL) with ice-bath cooling. The chosen indoles (1.0 g) were added as a dimethylformamide solution for preparation of corresponding indolecarbaldehydes. The resulting mixture was stirred at room temperature for one hour. The reaction mixture was quenched with chilled water, followed by the addition of aq Sodium hydroxide solution and refluxed at 100 C for 15 min. The reaction mixture was cooled to room temperature and maintained at 0 C overnight. The precipitates formed were collected and washed with water. After this, the -NH groups of different indolecarbaldehydes were protected with methyl, tosyl, benzyl, or methylsulfonyl by using corresponding halogenides (1.5 equiv) under different basic conditions, such as sodium hydride (1.5 equiv) using acetonitrile as a solvent. Then, the reaction of resulting N-protected indolecarbaldehydes (1.0 g) with nitromethane (5 mL) in the presence of 30 mol % of ammonium acetate as the catalyst to furnish the desired indolylnitroalkenes.9
	With trichlorophosphate; at 0 - 60℃; for 6.5h;	General procedure: A solution of indole (1.71 mmol) in dimethyl formamide (1 ml) was added to a cooled solutionof trichlorophosphate (1.88 mmol) in dimethyl formamide (1 ml) and stirred at room temperature for30 min and allowed to stir for 6 h at 60 C. The reaction mixture was allowed for cooling and pouredinto ice-cold water and added dropwise to an ice-cold solution of 2M NaOH. The suspension wasextracted with ethylacetate, the combined organic extract was concentrated to dryness to yield desiredindole-3-carboxaldehyde.

References: [1]Marine Drugs,2014,vol. 12,p. 1757 - 1772.
[2]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3146 - 3154.
[3]Synlett,2022,vol. 33,p. 259 - 263.
[4]Patent: US2018/244653,2018,A1 .Location in patent: Paragraph 0212.
[5]ACS Catalysis,2021,vol. 11,p. 4670 - 4681.
[6]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4783 - 4792.
[7]Tetrahedron Letters,2012,vol. 53,p. 2222 - 2225.
[8]Tetrahedron,2016,vol. 72,p. 8042 - 8049.
[9]Bioorganic Chemistry,2019,vol. 92.
[10]Molecules,2021,vol. 26.

2
[ 487-89-8 ]
[ 72527-73-2 ]
[ 114144-17-1 ]

References: [1]Heterocycles,1992,vol. 34,p. 219 - 223.

3
[ 114144-17-1 ]
4-chloro-5-iodo-3-indolecarboxaldehyde [ No CAS ]

References: [1]Heterocycles,1987,vol. 26,p. 2817 - 2822.

4
[ 114144-17-1 ]
4-bromo-5-iodo-3-indolecarboxaldehyde [ No CAS ]

References: [1]Heterocycles,1987,vol. 26,p. 2817 - 2822.

5
[ 114144-17-1 ]
4,5-diiodo-3-indolecarboxylate [ No CAS ]

References: [1]Heterocycles,1987,vol. 26,p. 2817 - 2822.

6
[ 61995-51-5 ]
[ 114144-17-1 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3146 - 3154.

7
[ 114144-16-0 ]
[ 114144-17-1 ]

References: [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 3146 - 3154.

8
[ 161892-02-0 ]
[ 114144-17-1 ]
(Z)-3-ethyl-2-imino-5-[(5-iodo-1H-indol-3yl)methylene]-1-methylimidazolidin-4-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 4783 - 4792.

9
[ 16066-91-4 ]
[ 100-61-8 ]
[ 114144-17-1 ]

References: [1]Chemical Communications,2012,vol. 48,p. 5187 - 5189.
[2]Journal of the American Chemical Society,2011,vol. 133,p. 11924 - 11927.

10
[ 114144-17-1 ]
[ 16066-91-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With perchloric acid adsorbed on silica gel; anthranilic acid amide; In acetonitrile; at 80℃; for 6h;	General procedure: Solid acid catalyst (50% w/w) was added to the solution of indole-3-carboxaldehydes 1a-1h or azaindole-3-carboxaldehyde 6 (1 mmol) and anthranilamide 2a (1 mmol) in acetonitrile (6 mL). The reaction mixture was allowed to stir for 6-24 h at room temperature or at reflux temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, it was allowed to cool and catalyst was recovered by filtration. The filtrate was concentrated to get crude products which after silica gel (No.100-200) column chromatography gave deformylated products 4a-4h or 5 in 25-90% yield.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 2222 - 2225.

11
[ 114144-17-1 ]
[ 28144-70-9 ]
2-(5-iodo-1H-indol-3-yl)quinazolin-4(3H)-one [ No CAS ]