676273-39-5|3-Iodo-1-tosyl-1H-indole-5-carbonitrile| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 676273-39-5 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 676273-39-5 ]

CAS No. :	676273-39-5
Formula :	C₁₆H₁₁IN₂O₂S
M.W :	422.24
SMILES Code :	N#CC1=CC2=C(N(S(=O)(C3=CC=C(C)C=C3)=O)C=C2I)C=C1
MDL No. :	MFCD13177481
InChI Key :	IUOBIBLYALVHRN-UHFFFAOYSA-N
Pubchem ID :	21955913

Safety of [ 676273-39-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 676273-39-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	22
Num. arom. heavy atoms	15
Fraction Csp3	0.06
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	93.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	71.24 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.8
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	3.96
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.74
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.	3.59
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	3.28
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.68

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-5.33
Solubility	0.002 mg/ml ; 0.00000473 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-5.16
Solubility	0.00294 mg/ml ; 0.00000697 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-6.23
Solubility	0.000251 mg/ml ; 0.000000594 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly 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	No
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	Yes
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	Yes
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.	-6.06 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	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<2.0
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)	2.96

Application In Synthesis of [ 676273-39-5 ]

* 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 [ 676273-39-5 ]

[ 676273-39-5 ] Synthesis Path-Downstream 1~35

1
[ 1092114-59-4 ]
[ 98-59-9 ]
[ 676273-39-5 ]

Yield	Reaction Conditions	Operation in experiment
95.5%		Preparation of compound 69b: 3-iodo-l-tosyl-l/7-indole-5-carbonitrileTo a solution of 3-iodo-l//-indole-5-carbonitrile (2 g, 7.40 mmol) in DMF (20 mL) was added 60% NaH (538 mg, 22.38 mmol) portion wise at 0 C and the reaction was stirred for 10 min RT. To the above mixture at 0 C, p-TsCl (2.2 g, 11.19 mmol) solution in DMF (4 mL) was added and stirred for further 2 h at RT. The reaction was quenched with ice cold H20 (20 mL). The resulting suspension was filtered and the solid was washed with H20 (10 mL) and dried. The crude was purified with silica gel chromatography (eluent: 20% EtOAc in petroleum ether) to afford 3-iodo-l-tosyl-l//-indole-5-carbonitrile (3.0 g, 95.5%) as an off brown solid. .H NMR (400MHz, DMSO-d6): delta 8.30 (s, 1H), 8.13 (d, J=8.8Hz, 1H), 7.98 (d, J=8.4Hz, 2H), 7.87-7.81 (m, 2H), 7.43 (d, J=8.0Hz, 2H), 2.32 (s, 3H).
95%		Compound 14 (22 g) was taken in dry THF (200 ml) and cooled to 0C and added NaH portion wise under stirring. After 30 minutes, tosyl chloride was added portion wise and the reaction mixture was stirred at RT for 3 hr and reaction was monitored by TLC. Reaction was quenched with saturated ammonium chloride solution and diluted with ethyl acetate. Aqueous layer was extracted with ethyl acetate and the combined organic layer was again washed with water and brine. Organic layer was dried over sodium sulphate and concentrated under vacuum. Ethyl ac- etate was evaporated to minimum quantity and was diluted with heptane and stirred for 1hr. A solid was obtained which was filtered and dried under vacuum.33 g of the pure solid compound 15 was obtained. 1H NMR (300 MHz, DMSO-d6) delta 8.31 (s, 1H), 8.13 (d, J = 8.6 Hz, 1H), 7.99 (d, J = 8.4 Hz, 2H), 7.91- 7.78 (m, 2H), 7.44 (d, J = 8.2 Hz, 2H), 2.34 (s, 3H).
91%	With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dichloromethane; at 20℃;Inert atmosphere;	Example 2 Synthesis of 3-iodo-1-tosyl-1H-indole-5-carbonitrile (V) [0062] 3-iodo-1H-indole-5-carbonitrile (V), obtained as described in Example 1 (8.7 g, 32.5 mmol), NaOH (2.1 g, 52.5 mmol), triethylbenzylammonium chloride (0.7 g, 3.1 mmol) and tosyl chloride (6.7 g, 35.1 mmol) are suspended in CH2Cl2 (260 mL) under inert atmosphere, and the reaction mixture is maintained under stirring at ambient temperature overnight. The mixture is treated with water and the phases are separated. The organic phase is further washed with water and a saturated solution of NaCl, then dried on Na2SO4, filtered and concentrated at low pressure. Product (V) is thus obtained as a solid (12.5 g) with a yield of 91%. [0063] 1H-NMR (400 MHz, CDCl3), delta: 8.02 (1H, d, J=8.4 Hz); 7.78-7.54 (3H, m); 7.69 (1H, s); 7.58 (1H, d, J=8.4 Hz); 7.26 (2H; d, J=8.0 Hz); 2.34 (3H, s).

With N-ethyl-N,N-diisopropylamine; In acetonitrile; for 1h;

5-cyanoindole (4.0 g, 28.1 mMol) was dissolved in DMF (20 mL) and potassium hydroxide (4.74 g, 84.4 mMol) was added. The reaction was cooled in a water bath at 10 C. and iodine (7.12 g, 28.1 mMol) was added. After stirring for 30 min the reaction was poured into water (100 mL) with sodium thiosulfate (2 g). The resulting solid 5-cyano-3-iodo-lindole was collected by filtration and recrystallized from ethyl acetate and hexanes.The crystals were dissolved in acetonitrile (60 mL) and N,N-diisopropylethylamine (5.64 mL, 32.3 mMol) and solid p-toluenesulfonyl chloride (6.17 g, 32.3 mMol) was added. After stirring for 1 h, the reaction was poured into water (100 mL) and the resulting solids were collected. The material was recrystallized from hot ethyl acetate/hexanes to provide the product as white needles (7.92 g, 67%): 1H NMR (400 MHz, CDCl3) delta 8.06 (1H, d, J=9.2 Hz), 7.79 (3H, m), 7.73 (1H, d, J=1.5 Hz), 7.61 (1H, dd, J=8.6, 1.5 Hz), 7.29 (2H, d, J=8.5 Hz), 2.38 (3H, s); MS m/e 454.9 (M+Na).

References: [1]Patent: WO2012/129338,2012,A1 .Location in patent: Page/Page column 193.
[2]Patent: WO2018/210659,2018,A1 .Location in patent: Page/Page column 162.
[3]Patent: US2014/275542,2014,A1 .Location in patent: Paragraph 0062; 0063.
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4031 - 4033.
[5]Patent: US2004/63768,2004,A1 .Location in patent: Page/Page column 9.

2
[ 676273-39-5 ]
[ 813-19-4 ]
[ 676273-40-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	palladium diacetate; triphenylphosphine; In DMF (N,N-dimethyl-formamide); at 60℃; for 0.666667h;	<strong>[676273-39-5]3-Iodo-1-(toluene-4-sulfonyl)-1H-indole-5-carbonitrile</strong> (5.0 g, 11.8 mMol) was added to a solution of bis(tributyltin) (6.27 mL, 12.4 mMol) in DMF (50 mL). Triphenyl phosphine (310 mg, 0.10 mMol) and palladium(II)acetate (133 mg, 0.59 mMol) were added and the reaction was heated to 60 C. for 40 min. The reaction was cooled in a water bath, then poured into brine (500 mL), and extracted with ethyl acetate (3×50 mL). The organic phase was dried with magnesium sulfate and the solvent was removed in vacuo. The reaction was purified by chromatography on silica gel with hexanes to remove tin byproducts followed by elution with ethyl acetate/hexanes (8%) to give the product as an off-white solid (5.67 g, 82%). 1H NMR (400 MHz, CDCl3) delta 8.02 (1H, d, J=8.6 Hz), 7.75 (3H, m), 7.52 (1H, dd, J=8.6, 1.5 Hz), 7.49 (1H, s), 7.24 (2H, m), 2.35 (3H, s), 1.05-1.82 (18H, m), 0.89 (9H, m); MS m/e 587.3 (M+H).

References: [1]Patent: US2004/63768,2004,A1 .Location in patent: Page/Page column 9.

3
[ 676273-39-5 ]
[ 98437-23-1 ]
[ 1027787-57-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	palladium diacetate; In N,N-dimethyl-formamide; at 60 - 90℃; for 5 - 16h;	Example 44 Preparation of QR-0311[00400] Compound QR-031 1 was prepared by reactions depicted in Scheme 50 below.[00401] The following General Procedure H was used. <n="125"/>General Procedure H[00402] Arylbromide or aryliodide (1 mmol). boric acid ( 1.2 mmol) andPd(OAc)2 (0.05 mmol) in DMF (5 niL) were stirred under argon at 60-90 0C for 5-16 h. The mixture was then cooled to room temperature, ethyl acetate (50 mL) was added and the mixture washed with brine 3 times (50 mL). The organic layer wasdried with MgSO4 and concentrated. The residue was purified by flash columnchromatography.100403] General Procedure H was used to yield 259 (63% yield). 1H NMR(CDCl3): 2.38 (s, 3H). 7.30 (d, 2H. J=8.4). 7.37-7.41 (m, 2H), 7.55 (s, I H), 7.64 (d.1 H. J=8.6), 7.82-8-7.86 (m, 4H), 7.96 (s. 1 H), 8.14 (d. 1 H, .1=8.6). 8.31 (s, 1 H).

References: [1]Patent: WO2008/58402,2008,A1 .Location in patent: Page/Page column 123-124.

4
[ 676273-39-5 ]
[ 122539-74-6 ]
[ 676273-41-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4031 - 4033.

5
[ 15861-24-2 ]
[ 676273-39-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium penicillin V; sodium thiosulfate; In N,N-dimethyl-formamide;	Example 1 Synthesis of 3-iodo-1H-indole-5-carbonitrile (V) 1H-indole-5-carbonitrile (5 g, 35.2 mmol), KOH (7.90 g, 141 mmol) and I2 (8.90 g, 35.2 mmol) are suspended in 25 mL of DMF under inert atmosphere. The reaction is maintained under stirring in the dark for 30 min. at 10C, and then treated with an 0.1M solution of Na2S2O3 (150 mL). The resulting suspension is maintained under stirring for 30 min, then filtered, and the resulting solid is washed with water and dried at 50C under vacuum to constant weight. Product (V) (9.0 g) is obtained as a white solid with a yield of 95%. 1H-NMR (400 MHz, CDCl3), delta: 8.78 (1H, bs); 7.80 (1H, s); 7.46-7.40 (3H, m).

References: [1]Patent: EP2778165,2014,A1 .Location in patent: Page/Page column.
[2]Patent: WO2012/129338,2012,A1 .
[3]Patent: US2014/275542,2014,A1 .
[4]Patent: WO2018/210659,2018,A1 .

6
[ 676273-39-5 ]
[ 1401345-96-7 ]