36193-65-4|1H-Indole-2-carbonitrile| Ambeed

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Quality Control of [ 36193-65-4 ] Purity: 97% SDS Specification

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Product Details of [ 36193-65-4 ]

CAS No. :	36193-65-4
Formula :	C₉H₆N₂
M.W :	142.16
SMILES Code :	N#CC(N1)=CC2=C1C=CC=C2
MDL No. :	MFCD00187566
InChI Key :	CBTITARLOCZPDU-UHFFFAOYSA-N
Pubchem ID :	3787599

Safety of [ 36193-65-4 ]

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

Computational Chemistry of [ 36193-65-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	43.01
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	39.58 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.42
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	2.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.04
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.	0.88
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	2.51
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.87

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.9
Solubility	0.178 mg/ml ; 0.00125 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.	-2.98
Solubility	0.15 mg/ml ; 0.00106 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	-3.34
Solubility	0.0644 mg/ml ; 0.000453 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.	-5.39 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)	1.55

Application In Synthesis of [ 36193-65-4 ]

* 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 [ 36193-65-4 ]

[ 36193-65-4 ] Synthesis Path-Downstream 1~35

1
[ 36193-65-4 ]
[ 63071-71-6 ]

References: [1]Journal of the Chemical Society,1956,p. 2853,2856.

2
[ 36193-65-4 ]
[ 117311-26-9 ]

References: [1]Journal of the Chemical Society,1956,p. 2853,2856.

3
[ 1670-84-4 ]
[ 36193-65-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	In P,P-dichlorophenylphosphine oxide;	b 2-Cyanoindole A solution of indole-2-carboxamide (3.02 g, 18.8 mmol) in dichlorophenylphosphine oxide (20 mL) was heated at 80 C. overnight. The cooled reaction mixture was then poured over 100 mL ice and the pH was adjusted to 11 with 50% aqueous sodium hydroxide. Extraction with ethyl acetate followed by concentration in vacuo gave an off-white solid which was purified by silica gel chromatography (1% MeOH/CH2 Cl2) to yield the title compound (2.41 g, 90%): 1 H NMR (400 MHz, DMSO-d6) delta 7.68 (d, 1H), 7.46 (d, 1H), 7.36 (s, 1H), 7.34 (t, 1H), 7.14 (t, 1H).
66.4%	With trichlorophosphate; In chloroform; for 2h;Heating / reflux;	Ib) lH-Indole-2-carbonitrile; A mixture of 8.96 g (56 mmol) of lH-indole-2-carboxylic acid amide, 26.0 ml (279 mmol) of phosphorus oxychloride and 230 ml of chloroform is refluxed for 2h. The reaction mixture is cooled to 20 C, poured into 100 ml of water and stirred for Ih. After separation the organic layer is dried over sodium sulfate and concentrated. The residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and hexane-ethyl acetate = 4: 1 as eluent to yield 5.28 g (66.4 %) of the title compound. Mp.: 94-95 C.
		To a cooled solution of indole-2-carboxylic acid(2.0 g, 12.4 mmol) in 60 mL of anhydrous Et20 was added 1.9 mL of SOCl2 (26 mmol). After stirring for 40 min at RT, the ether was removed under reduced pressure at a temperature not exceeding 35 C. The obtained acyl chloride was dissolved in 40 mL of anhydrous Et20 and the resulting solution was added immediately to a stirred solution of liquid ammonia in 80 ml of Et20. The reaction mixture was stirred at RT for 24 h. The solvent was then evaporated under reduced pressure, and the white indole-2-carboxamide was crystallized from 50% aq EtOH and dried in air, after which it was dissolved in POCI3 and heated under reflux for 5 min. The cooled solution was poured onto crushed ice and aq NH4OH was added to maintain a basic pH. The aqueous mixture was extracted with Et20, the extracts were dried over Na2S04 and evaporated. The brown indole-2-carbonitrile 60a (63.3% overall yield from indole-2-carboxylic acid) was obtained. 1H NMR (500 MHz, CDC13) delta 8.56 (br, s, 1 H), 7.68 (d, 1 H, J = 8.0 Hz), 7.43-7.34 (m, 2 H), 7.24-7.21 (m, 2 H). MS (ESI) m/z 144.0 (M + H)+, 140.8 (M -H)-.

References: [1]Patent: US5977101,1999,A .
[2]Chemical Communications,2007,p. 301 - 303.
[3]Patent: WO2006/10965,2006,A1 .Location in patent: Page/Page column 13.
[4]Journal of the Chemical Society,1956,p. 2853,2856.
[5]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5439 - 5441.
[6]Journal of Organic Chemistry,2002,vol. 67,p. 9276 - 9287.
[7]Journal of Medicinal Chemistry,2011,vol. 54,p. 4678 - 4693.
[8]Patent: WO2011/109059,2011,A1 .Location in patent: Paragraph 0038; 00329.
[9]Journal of Chemical Sciences,2013,vol. 125,p. 71 - 83.

4
[ 36193-65-4 ]
[ 58656-98-7 ]
1-[4-(tert-butoxycarbonyl)phenyl]-2-cyanoindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dimethyl sulfoxide;	A Preparation of (26) where R10 is 2-Cyanoindole A mixture of 3.0 g (0.02 mol) of <strong>[36193-65-4]2-cyanoindole</strong>, 4.2 g (0.02 mol) of tert-butyl-4-fluorobenzoate, and 5.5 g (0.04 mol) of potassium carbonate in 30 ml dimethyl sulfoxide was heated at 110 C. for 48 hours. The reaction was poured onto ice-water and extracted twice with ethyl acetate. The organic extracts were combined, washed with water and dried over magnesium sulfate. Evaporation yielded a dark oil which was flash chromatographed on silica gel, eluding with ethyl acetate-hexane 1:9 to give 3.6 g (0.011 mol) of 1-[4-(tertbutoxycarbonyl)phenyl]-<strong>[36193-65-4]2-cyanoindole</strong> as an oil.

References: [1]Synthetic Communications,1994,vol. 24,p. 123 - 129.
[2]Patent: US5380739,1995,A .

5
[ 36193-65-4 ]
[ 98-88-4 ]
[ 90539-84-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 405 - 412.

6
[ 36193-65-4 ]
[ 98-09-9 ]
[ 116325-35-0 ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 7188.

7
[ 36193-65-4 ]
[ 51796-65-7 ]
[ 51796-62-4 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 5316 - 5319.

8
[ 54698-11-2 ]
[ 151-50-8 ]
[ 36193-65-4 ]
[ 16712-55-3 ]

References: [1]Heterocycles,1993,vol. 35,p. 99 - 104.

9
[ 54698-11-2 ]
[ 36193-65-4 ]
[ 16712-55-3 ]

References: [1]Heterocycles,1993,vol. 35,p. 99 - 104.

10
[ 51991-49-2 ]
[ 36193-65-4 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 5316 - 5319.

11
[ 594-19-4 ]
[ 116325-35-0 ]
[ 36193-65-4 ]
1-(1H-indol-2-yl)-2,2-dimethylpropan-1-one [ No CAS ]

References: [1]Journal of the Chinese Chemical Society,1993,vol. 40,p. 571 - 580.

12
[ 116325-35-0 ]
[ 36193-65-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h;Reflux;	To a solution of N-phenylsulfonyl-2-cyanoindole (3, 2.0 g,7.1 mmol, 1 equiv) in THF (30 mL) was added a solution of TBAF (10.6 mL,1.0 M in THF, 1.5 equiv). After heating at reflux for 3 h, the mixture was cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and water (100 mL) and the layers separated. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo to an off-white solid. The product was purified by flash chromatography(silica gel, hexanes:EtOAc 4:1) to afford 4 as a white solid, 827 mg (82%); 1HNMR (300 MHz, CDCl3) d 8.66 (br s, 1H), 7.68 (d, 1H, J = 8.1 Hz), 7.44-7.36 (m,2H), 7.25-7.20 (m, 2H).

References: [1]Journal of the Chinese Chemical Society,1993,vol. 40,p. 571 - 580.
[2]Tetrahedron Letters,2013,vol. 54,p. 6142 - 6145.

13
[ 74845-01-5 ]
[ 36193-65-4 ]

References: [1]Journal of Organic Chemistry,1980,vol. 45,p. 4767 - 4769.

14
C₄H₈NS⁽¹⁺⁾*BF₄^(1-) [ No CAS ]
Trimethyl-[2-(toluene-4-sulfonylamino)-benzyl]-ammonium [ No CAS ]
[ 36193-65-4 ]
N-2-(4-methylphenylsulfonyl)methylphenyl-4-methylbenzenesulfonamide [ No CAS ]

References: [1]Heterocycles,1996,vol. 43,p. 2397 - 2407.

15
[ 36193-65-4 ]
[ 3958-60-9 ]
1-(2-Nitro-benzyl)-1H-indole-2-carbonitrile [ No CAS ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 359 - 362.

16
1-(2-Nitro-benzyl)-1H-indole-2-carbonitrile [ No CAS ]
[ 36193-65-4 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 359 - 362.

17
[ 26340-49-8 ]
[ 119072-55-8 ]
[ 36193-65-4 ]

References: [1]Chemical Communications,1999,p. 1761 - 1762.

Yield	Reaction Conditions	Operation in experiment
55%		B. 1H-Indole-2-carbonitrile The title A compound (8.5 g, 53.1 mmol) was suspended in 1,4 dioxane (110 mL) and pyridine (10.74 mL). The solution was then cooled to less than 10 C. and trifluoroacetic anhydride (11.99 mL, 84.9 mmol) was slowly added to the reaction. Upon full addition, the reaction was stirred at room temperature for 18 hours. The reaction was then slowly quenched with water and extracted with ethyl acetate and the organic phase was dried and concentrated. The crude solid was purified by flash chromatography (silicon dioxide, 95:5 hexane:ethyl acetate) to provide pure nitrile (4.16 g, 55% over 2 steps).
		B. 1H-Indole-2-carbonitrile The title A compound (8.5 g, 53.1 mmol) was suspended in 1,4 dioxane (110 mL) and pyridine (10.74 mL). The solution was then cooled to less than 10 C. and trifluoroacetic anhydride (11.99 mL, 84.9 mmol) was slowly added to the reaction. Upon full addition, the reaction was stirred at room temperature for 18 hours. The reaction was then slowly quenched with water and extracted with ethyl acetate and the organic phase was dried and concentrated. The crude solid was purified by flash chromatography (silicon dioxide, 95:5 hexane:ethyl acetate) to provide pure nitrile (4.16 g, over 2 steps).

19
[ 116325-35-0 ]
Me₂CuLi [ No CAS ]
[ 36193-65-4 ]
[ 4264-35-1 ]

References: [1]Journal of the Chinese Chemical Society,1993,vol. 40,p. 571 - 580.

20
[ 36193-65-4 ]
[ 30354-18-8 ]
3-dimethylaminomethyl-1H-indole-2-carbonitrile [ No CAS ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 1671 - 1679.

21
[ 36193-65-4 ]
[ 51796-65-7 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 9276 - 9287.
[2]Journal of Chemical Sciences,2013,vol. 125,p. 71 - 83.

22
[ 498-66-8 ]
[ 490039-75-3 ]
[ 36193-65-4 ]
N-benzenesulfonyl-6-oxo-6a,7,8,9,10,10a-hexahydro-7,10-methano-6H-indeno[2,1-b]indole [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 9276 - 9287.

23
[ 127280-17-5 ]
[ 36193-65-4 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 9276 - 9287.

24
[ 51796-65-7 ]
[ 36193-65-4 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 9276 - 9287.
[2]Journal of Organic Chemistry,2002,vol. 67,p. 9276 - 9287.

25
[ 36193-65-4 ]
[ 64-17-5 ]
[ 117311-26-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride; at 20℃; for 2h;	Ic) lH-Indole-2-carboximidic acid ethyl ester hydrochloride; To a solution of 20 ml of saturated hydrochloric acid hi ethanol 2.23 g (15.7 mmol) oflH-<strong>[36193-65-4]indole-2-carbonitrile</strong> is added. The reaction mixture is stirred at 20 C for 2 h, thenconcentrated and the residue is crystallized with ether to yield 3.1 g (82 %) of the title compound.Mp.: 170 C .

References: [1]Patent: WO2006/10965,2006,A1 .Location in patent: Page/Page column 13.
[2]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5439 - 5441.

26
[ 36193-65-4 ]
[ 687-47-8 ]
[ 878020-62-3 ]

References: [1]Russian Chemical Bulletin,2005,vol. 54,p. 226 - 230.

27
[ 36193-65-4 ]
[ 82027-15-4 ]
[ 878020-61-2 ]

References: [1]Russian Chemical Bulletin,2005,vol. 54,p. 226 - 230.

28
[ 36193-65-4 ]
[ 535-11-5 ]
[ 878020-60-1 ]