[ CAS No. 21344-24-1 ]

Name: 21344-24-1|5-Bromothieno[2,3-b]pyridine|98%
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Quality Control of [ 21344-24-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 21344-24-1 ]

CAS No. :	21344-24-1	MDL No. :	MFCD18254753
Formula :	C₇H₄BrNS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YMOORGYWRBQPDZ-UHFFFAOYSA-N
M.W :	214.08	Pubchem ID :	12885487
Synonyms :

Calculated chemistry of [ 21344-24-1 ]

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 :	41.13 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.55 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	2.89
Log Po/w (WLOGP) :	3.06
Log Po/w (MLOGP) :	2.27
Log Po/w (SILICOS-IT) :	3.87
Consensus Log Po/w :	2.84

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.65
Solubility :	0.0475 mg/ml ; 0.000222 mol/l
Class :	Soluble
Log S (Ali) :	-3.41
Solubility :	0.0825 mg/ml ; 0.000386 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.83
Solubility :	0.0317 mg/ml ; 0.000148 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 21344-24-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 21344-24-1 ]
Downstream synthetic route of [ 21344-24-1 ]

[ 21344-24-1 ] Synthesis Path-Upstream 1~5

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

Yield	Reaction Conditions	Operation in experiment
53%	With copper(ll) bromide; isopentyl nitrite In acetonitrile at 20℃;	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. R^f=0.80) to give the title compound (1.03 g, yield, 53.0percent). 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)⁺.

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

2
[ 1242336-81-7 ]
[ 21344-24-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 150℃;	(C) To a solution of 971 5-bromothieno[2,3-b]pyridine-2-carboxylic acid (6.6 g, 25.6 mmol) in 973 DMA (50 mL) was added 974 DBU (12.8 g, 84.1 mmol) and the resulting mixture was stirred at 150° C. overnight. After cooling to rt, the reaction was quenched with 444 H₂O (100 mL) and the resulting mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na₂SO₄), filtered and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (0-10percent EtOAc/petroleum ether) to afford 975 5-bromothieno[2,3-b]pyridine (3.3 g, 60percent), as a white solid. LC/MS: mass calcd. for C₇H₄BrNS: 212.92, found: 213.8, 215.8 [M+H, M+H+2]⁺.

Reference： [1] Patent: US2017/291908, 2017, A1, . Location in patent: Paragraph 0760

3
[ 56267-50-6 ]
[ 2065-75-0 ]
[ 21344-24-1 ]

Yield	Reaction Conditions	Operation in experiment
3%	With hydrogenchloride In ethanol at 105℃; for 24 h; 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 2percent MeOH in DCM to give 5-bromothieno[2,3-b]pyridine as a yellow solid (90 mg, 3percent). 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)+.

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

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

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

5
[ 21344-24-1 ]
[ 73183-34-3 ]
[ 1034579-02-6 ]

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

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

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

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

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

Reference： [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)+.

Reference： [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 ]

Reference： [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.

Reference： [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).

Reference： [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).

Reference： [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)+.

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

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

Yield	Reaction Conditions	Operation in experiment
60%	With N,N-dimethyl acetamide; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 150.0℃;	(C) To a solution of 971 5-bromothieno[2,3-b]pyridine-2-carboxylic acid (6.6 g, 25.6 mmol) in 973 DMA (50 mL) was added 974 DBU (12.8 g, 84.1 mmol) and the resulting mixture was stirred at 150 C. overnight. After cooling to rt, the reaction was quenched with 444 H2O (100 mL) and the resulting mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography (0-10% EtOAc/petroleum ether) to afford 975 5-bromothieno[2,3-b]pyridine (3.3 g, 60%), as a white solid. LC/MS: mass calcd. for C7H4BrNS: 212.92, found: 213.8, 215.8 [M+H, M+H+2]+.

Reference： [1]Patent: US2017/291908,2017,A1 .Location in patent: Paragraph 0760

11
[ 21344-24-1 ]
5-cyclopropylthieno[2,3-b]pyridine-2-carbaldehyde [ No CAS ]