21344-24-1|5-Bromothieno[2,3-b]pyridine| Ambeed

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Quality Control of [ 21344-24-1 ] Purity: 98% SDS Specification

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Product Details of [ 21344-24-1 ]

CAS No. :	21344-24-1
Formula :	C₇H₄BrNS
M.W :	214.08
SMILES Code :	BrC1=CN=C2C(C=CS2)=C1
MDL No. :	MFCD18254753
InChI Key :	YMOORGYWRBQPDZ-UHFFFAOYSA-N
Pubchem ID :	12885487

Safety of [ 21344-24-1 ]

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

Computational Chemistry of [ 21344-24-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	47.32
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.13 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.12
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	2.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.06
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.	2.27
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	3.87
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.84

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.65
Solubility	0.0475 mg/ml ; 0.000222 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.	-3.41
Solubility	0.0825 mg/ml ; 0.000386 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	-3.83
Solubility	0.0317 mg/ml ; 0.000148 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.	-5.55 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	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)	1.95

Application In Synthesis of [ 21344-24-1 ]

* 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 [ 21344-24-1 ]

[ 21344-24-1 ] Synthesis Path-Downstream 1~18

1
[ 21344-24-1 ]
[ 143-33-9 ]
[ 21344-31-0 ]

References: [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 773 - 778.

2
[ 21344-24-1 ]
[ 21344-47-8 ]

References: [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 773 - 778.

3
[ 21344-28-5 ]
[ 21344-24-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 20.0℃;	Example 16E 5-Bromothieno[2,3-b]pyridine The product of Example 16D (1.35 g. 9.0 mmol) was treated with iso-amylnitrite (Aldrich. 2.10 g. 18.0 mmol) and CuBr2 (Aldrich, 4.03 g. 18.0 mmol) in MeCN (20 mL) at ambient temperature overnight. The reaction mixture was quenched with saturated NH4Cl (20 mL) and then extracted with EtOAc (350 mL). The combined extracts were washed with brine (230 mL) and concentrated. The residue was purified with chromatography (SiO2, EtOAc/hexane, v. 80/20. Rf=0.80) to give the title compound (1.03 g, yield, 53.0%). 1H NMR (300 MHz, CDCl3) 8 ppm 7.22 (d, J=6.10 Hz, 1H), 7.58 (d, J=6.10 Hz, 1H). 8.21 (d, J=2.37 Hz, 1H), 8.61 (d, J=2.0(3 Hz, 1H):MS (DCI/NH3) m/z 214 (M+1)+, 216 (M+1)+.

References: [1]Patent: US2008/153860,2008,A1 .Location in patent: Page/Page column 25.
[2]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 773 - 778.

5
[ 21344-35-4 ]
[ 21344-24-1 ]

References: [1]Journal of Heterocyclic Chemistry,1968,vol. 5,p. 773 - 778.

6
[ 21344-24-1 ]
[ 73183-34-3 ]
[ 1034579-02-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 85.0℃;	A mixture of the product, <strong>[21344-24-1]5-bromothieno[2,3-b]pyridine</strong>I from Part B (1 equiv), bispinacolatodiboron (1.2 equiv), PdCI2dppf (0.1 equiv), and potassium acetate (3 equiv) in dioxane was heated at 85 C until the reaction was deemed complete by TLC, HPLC, or LC-MS analysis. The reaction was allowed to cool to room temperature, filtered through a pad of celite, concentrated to dryness, treated with diethyl ether, filtered through a pad of celite, and then concentrated to afford the desired product, 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)thieno[2,3-b]pyridine.

References: [1]Patent: WO2010/118207,2010,A1 .Location in patent: Page/Page column 284-285.

7
5-bromo-2-(trimethylsilyl)thieno[2,3-b]pyridine [ No CAS ]
[ 21344-24-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In ethanol; at 65.0℃; for 1.0h;	The 5-bromo-2-(trimethylsilyl)thieno[2,3-b]pyridine from Part A (8.99 g, 31.4 mmol) was dissolved in ethano. (70 mL), followed by addition of K2CO3 (10.85g, 78.5 mmol). Reaction was stirred at 65 C for 1 hour. The reaction mixture was allowed to cool to 25 C, concentrated to dryness, and dissolved in EtOAc (150 mL). The solution was washed with H2O (80 mL), and brine (15OmL), dried over Na3SO4, filtered, and concentrated to yield white solid, 5-bromothieno[2,3-b]pyridine, 6.57 g (98%). 1H NMR (300 MHz, CDCI3) delta 8.60 (d, J = 2.2 Hz, 1 H), 8.16 (d, J = 2.2 Hz 1 H), 7.57 (d, J = 6.0 Hz 1 H), 7.21 (d, J = 6.0 Hz, 1 H).

References: [1]Patent: WO2010/118207,2010,A1 .Location in patent: Page/Page column 284.

8
[ 21344-24-1 ]
[ 1267856-37-0 ]
2-(4-(thieno[2,3-b]pyridin-5-yl)phenyl)-N-(5-(1-(trifluoromethyl)cyclopropyl)isoxazol-3-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; acetonitrile; at 100.0℃; for 0.5h;Inert atmosphere; Microwave irradiation;	Step 2: To a solution of <strong>[21344-24-1]5-bromothieno[2,3-b]pyridine</strong> (81 mg, 0.38 mmol), 2-(4- (4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyl)-N-(5 -(1- (trifluoromethyl)cyclopropyl)isoxazol-3-yl)acetamide from Step 1 of Example 9 (150 mg, 0.34 mmol) and 2M aqNa2CO3 (1 mL) in 7:1 CH3CN:H20 (4 mL) was added Pd(dppf)C12 dichloromethane complex (28 mg, 0.034 mmol) under N2. The reaction mixture was heated to 100 oC for 30 mm under microwave conditions. After cooling to rt, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by preparative reverse-phase HPLC to give 2-(4-(thieno [2,3 -b]pyridin-5 -yl)phenyl)-N-(5 -(1- (trifluoromethyl)cyclopropyl)isoxazol-3-yl)acetamide as a yellow solid (44 mg, 26%). 1H NMR (300 MHz, DMSO-d6) oe 11.40 (s, 1H), 8.85 (s, 1H), 8.51 (s, 1H), 7.92 (d, J= 5.7 Hz, 1H), 7.74 (d, J 7.8 Hz, 2H), 7.43-7.49 (m, 3H), 6.92 (s, 1H), 3.74 (s, 2H), 1.46-1.49 (m, 4H). LC-MS (ESI) m/z 444 (M+H).

References: [1]Patent: WO2015/31613,2015,A1 .Location in patent: Paragraph 000172.

9
[ 56267-50-6 ]
[ 2065-75-0 ]
[ 21344-24-1 ]

Yield	Reaction Conditions	Operation in experiment
3%	With hydrogenchloride; In ethanol; at 105.0℃; for 24.0h;Inert atmosphere;	To a solution of tert-butyl thiophen-2-ylcarbamate (3.0 g, 15 mmol) and 2-bromomalonaldehyde (2.57 g, 17 mmol) in EtOH (30 mL) was added concentrated HC1 (7.5 mL) under N2. The reaction mixture was heated to 105 oC for 24 h. After cooling to rt, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 2% MeOH in DCM to give 5-bromothieno[2,3-b]pyridine as a yellow solid (90 mg, 3%). 1H NMR (300 MHz, CDC13 8.60 (d, J = 2.1 Hz, 1H), 8.11 (d, J = 2.4 Hz, 1H), 7.55-7.60 (m, 1H), 7.19-7.22 (m, 1H). LC-MS (ESI) mlz 215 (M+H)+.

References: [1]Patent: WO2015/31613,2015,A1 .Location in patent: Paragraph 000171.

10
[ 1242336-81-7 ]
[ 21344-24-1 ]