[ CAS No. 57883-25-7 ] {[proInfo.proName]}

Name: 57883-25-7|3-Bromo-2-ethoxypyridine|95%
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SKU: A207390
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Quality Control of [ 57883-25-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 57883-25-7 ]

SDS Specification

Alternatived Products of [ 57883-25-7 ]

Product Details of [ 57883-25-7 ]

CAS No. :	57883-25-7	MDL No. :	MFCD00234309
Formula :	C₇H₈BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KLQBFCAXXZMOLZ-UHFFFAOYSA-N
M.W :	202.05	Pubchem ID :	10987308
Synonyms :

Calculated chemistry of [ 57883-25-7 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.24
TPSA :	22.12 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) :	-5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.35
Log Po/w (XLOGP3) :	2.21
Log Po/w (WLOGP) :	2.24
Log Po/w (MLOGP) :	1.65
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	2.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.8
Solubility :	0.322 mg/ml ; 0.0016 mol/l
Class :	Soluble
Log S (Ali) :	-2.31
Solubility :	0.992 mg/ml ; 0.00491 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.42
Solubility :	0.0777 mg/ml ; 0.000385 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 57883-25-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H227-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 57883-25-7 ]

* 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 [ 57883-25-7 ]
Downstream synthetic route of [ 57883-25-7 ]

[ 57883-25-7 ] Synthesis Path-Upstream 1~4

1
[ 36178-05-9 ]
[ 64-17-5 ]
[ 57883-25-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 3 h; Inert atmosphere	A 60percent dispersion of sodium hydride in mineral oil (7.4 g, 184.6 mmol) was suspended in anhydrous tetrahydrofuran (300 mL) under nitrogen. Absolute ethanol (10.0 mL, 170.4 mmol) was added dropwise at room temperature and the reaction mixture was stirred for 40 minutes at room temperature. 2-Fluoro-3-bromopyridine (25.0 g, 142.0 mmol) was added and the reaction mixture was stirred for 3 hours at room temperature. Water (250 mL) was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (2 x 200 mL). The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a light yellow oil (31 .5 g, 84percent). ¹H NMR (400MHz, CDCl₃): δ ppm 1.43 (m, 3H), 4.43 (m, 2H), 6.74 (m, 1 H), 7.79 (m, 1 H), 8.07 (m, 1 H). LCMS Rt = 2.45 minutes MS m/z 203 [MH]⁺

Reference： [1] Patent: WO2013/93688, 2013, A1, . Location in patent: Page/Page column 45

2
[ 52200-48-3 ]
[ 141-52-6 ]
[ 57883-25-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Reflux	3-Bromo-2-chloropyridine (10.0 g, 52.0 mmol) was dissolved in ethanol (100 mL) and a solution of sodium ethylate in ethanol (70.8 mL, 21 percent) was added. The mixture was heated to reflux overnight. The solvent was then removed in vacuo and the residue was dissolved in ethyl acetate and washed with satd. aqueous ammonium chloride solution. The organic layer was dried over sodium sulphate, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 10: 1 ) to yield 7.26 g (69percent) of an yellow oil. ¹H-NMR (400MHz, DMSO-d₆): δ [ppm]= 1 .34 (t, 3H), 4.37 (q, 2H), 6.93 (dd, 1 H), 8.02 (dd, 1 H), 8.15 (dd, 1 H).

Reference： [1] Patent: WO2014/195274, 2014, A1, . Location in patent: Page/Page column 75-76

3
[ 52200-48-3 ]
[ 64-17-5 ]
[ 141-52-6 ]
[ 57883-25-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Reflux	Intermediate [Example Int22.13-bromo-2-ethoxypyridine3-Bromo-2-chloropyridine (10.0 g) was dissolved in ethanol (100 mL) and a solution of sodium ethylate in ethanol (70.8 mL, 21 percent) was added. The mixture was heated to reflux overnight. The solvent was then removed in vacuo and the residue was dissolved in ethyl acetate and washed with satd. aqueous ammonium chloride solution. The organic layer was dried over sodium sulphate, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 10: 1 ) to yield 7.26 g (69percent) of an yellow oil.¹ H-NMR (400MHz, DMSO-d₆): δ [ppm]= 1 .34 (t, 3H), 4.37 (q, 2H), 6.93 (dd, 1 H), 8.02 (dd, 1 H), 8.15 (dd, 1 H).

Reference： [1] Patent: WO2011/64328, 2011, A1, . Location in patent: Page/Page column 105

4
[ 57883-25-7 ]
[ 73183-34-3 ]
[ 848243-23-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 95℃; for 6 h; Inert atmosphere	A suspension of 3-bromo-2-ethoxypyridine (Preparation 1 1 , 28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol), and potassium acetate (41 .8 g, 425.9 mmol) in DMSO (100 mL) was degassed with nitrogen and [1 ,1 '- bis(diphenylphosphinoferrocene]dichloro palladium (II) (5.8 g, 7.93 mmol) was added and the reaction mixture was stirred for 6 hours at 95 °C. The reaction mixture was filtered through a pad of Arbocel which was washed with ethyl acetate (500 mL). The filtrate was concentrated in vacuo and the crude material was purified by silica gel column chromatography eluting with 50percent ethyl acetate in cyclohexane to afford the title compound as a red oil (34.4g, 74percent). ¹H NMR (400MHz, CDCl₃): δ ppm 1 .35 (s, 12H), 1 .39 (m, 3H), 4.37 (m, 2H), 6.81 (m, 1 H), 7.89 (m, 1 H), 8.19 (m, 1 H). LCMS Rt = 3.27 minutes MS m/z 250 [MH]⁺

Reference： [1] Patent: WO2013/93688, 2013, A1, . Location in patent: Page/Page column 44-45

[ 57883-25-7 ] Synthesis Path-Downstream 1~37

1
[ 57883-25-7 ]
[ 565-80-0 ]
1-(2-Ethoxy-4-isopropyl-pyridin-3-yl)-2-methyl-propan-1-one [ No CAS ]
2-(2-Ethoxy-pyridin-4-yl)-2,4-dimethyl-pentan-3-one [ No CAS ]
1,8-Diethoxy-9-isopropyl-10,10-dimethyl-9,10-dihydro-2,7-diaza-anthracen-9-ol [ No CAS ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,1996,vol. 52,p. 2097 - 2100

2
[ 110-89-4 ]
[ 57883-25-7 ]
[ 46410-19-9 ]
2'-Ethoxy-3,4,5,6-tetrahydro-2H-[1,3']bipyridinyl [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2113 - 2129

3
[ 110-91-8 ]
[ 57883-25-7 ]
4-(2-Ethoxy-pyridin-4-yl)-morpholine [ No CAS ]
4-(2-Ethoxy-pyridin-3-yl)-morpholine [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2113 - 2129

4
[ 57883-25-7 ]
[ 105-04-4 ]
N-(2-Ethoxy-pyridin-4-yl)-N,N',N'-triethyl-ethane-1,2-diamine [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2113 - 2129

5
[ 57883-25-7 ]
[ 142-84-7 ]
2-ethoxy-3-dipropylaminopyridine [ No CAS ]
2-ethoxy-4-dipropylaminopyridine [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2113 - 2129

6
[ 57883-25-7 ]
[ 109-89-7 ]
3-ethoxy-4-diethylaminopyridine [ No CAS ]
2-ethoxy-4-diethylaminopyridine [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2113 - 2129

7
[ 57883-25-7 ]
[ 108-18-9 ]
2-ethoxy-4-diisopropylaminopyridine [ No CAS ]
2-ethoxy-3-diisopropylaminopyridine [ No CAS ]

Reference： [1]Heterocycles,1997,vol. 45,p. 2113 - 2129

9
[ 57883-25-7 ]
[ 850034-48-9 ]
[ 850034-49-0 ]

Yield	Reaction Conditions	Operation in experiment
44%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); johnphos; at 150.0℃; for 1.0h;microwave irradiation;	A solution of tris(dibenzylideneacetone)dipalladium(0) (12 mg, 13 mumol) and 2-(di-tert-butylphosphino)biphenyl (12.0 mg, 40 mumol) in anhydrous toluene (5 mL) was degassed with argon for 15 min at room temperature, then <strong>[57883-25-7]3-bromo-2-ethoxypyridine</strong> (33 mg, 0.16 mmol) was added. Upon further degassing, N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-amino-7-trifluoromethyl-pyrazino[2, 1-a]isoindol-6(2H)-one (66 mg, 0.18 mmol) and sodium tert-butoxide (26 mg, 0.27 mmol) were added. The mixture was degassed a final time and then subjected to microwave conditions (150 W, 150 C.) for 1 h. Upon cooling to room temperature, the mixture was filtered through a pad of diatomaceous earth and the pad was washed with EtOAc (100 mL). The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (silica gel, 5-60% Et2O/hexanes) to provide the corresponding N-linked oxoisoindole (35 mg) in 44% yield. A solution of the Boc-protected oxoisoindole in CH2Cl2 (10 mL) at -10 C. was treated with TFA (3 mL) and stirred for 2.5 h. Upon concentration in vacuo, the residue was purified by preparative HPLC (Varian Dynamax C18 column, 10-100% CH3CN/H2O with 0.05% TFA) followed by trituration of the combined fractions with CH2Cl2/Et2O/hexanes to provide the product (9 mg, 25%) as a yellow solid: MS (APC1) 393 (M+H)

Reference： [1]Patent: US2005/80074,2005,A1 .Location in patent: Page/Page column 41

10
[ 52200-48-3 ]
[ 64-17-5 ]
[ 141-52-6 ]
[ 57883-25-7 ]

Yield	Reaction Conditions	Operation in experiment
69%	Reflux;	Intermediate [Example Int22.13-bromo-2-ethoxypyridine3-Bromo-2-chloropyridine (10.0 g) was dissolved in ethanol (100 mL) and a solution of sodium ethylate in ethanol (70.8 mL, 21 %) was added. The mixture was heated to reflux overnight. The solvent was then removed in vacuo and the residue was dissolved in ethyl acetate and washed with satd. aqueous ammonium chloride solution. The organic layer was dried over sodium sulphate, and the solvent was evaporated. The crude product was purified by column chromatography on silica gel (eluent: cyclohexane / ethyl acetate 10: 1 ) to yield 7.26 g (69%) of an yellow oil.1 H-NMR (400MHz, DMSO-d6): delta [ppm]= 1 .34 (t, 3H), 4.37 (q, 2H), 6.93 (dd, 1 H), 8.02 (dd, 1 H), 8.15 (dd, 1 H).

Reference： [1]Patent: WO2011/64328,2011,A1 .Location in patent: Page/Page column 105

11
[ 57883-25-7 ]
[ 1309682-22-1 ]
[ 1309681-06-8 ]

Yield	Reaction Conditions	Operation in experiment
63%	With sodium t-butanolate;chloro(2-dicyclohexylphosphino-2?,4?,6?-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) methyl tert-butyl ether; XPhos; In toluene; at 130.0℃; for 6.0h;	Example 1 1.0034-{2-[(2-ethoxypyridin-3-yl)amino][1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl}-N- 2,2,2-trifluoroethyl)benzamide4-(2-Amino[1 ,2,4]triazolo[1 ,5-a]pyridin-6-yl)-N-(2,2,2-trifluoroethyl)benzamide Int9.2 (100 mg), <strong>[57883-25-7]3-bromo-2-ethoxypyridine</strong> Int22.1 (72 mg), chloro(2-dicyclo- hexylphosphino-2',4',6'-tri-i-propyl-1 , 1 '-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) (22 mg), X-Phos (14 mg), and sodium tert-butoxide (52.3 mg) were pre-mixed, and degassed toluene (2.2 mL) was added. The mixture was heated for 6h to 130 C. Subsequently, DCM was added, and the mixture was washed with satd. aqueous Na2C03 solution. The organic layer was dried over Na2S04, and the solvent was evaporated. The crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate / ethanol gradient 50: 1 to 20: 1 ) to yield 86 mg (63%) of the title compound.1 H-NMR (400MHz, DMSO-d6): delta [ppm]= 1 .41 (t, 3H), 4.08 - 4.18 (m, 2H), 4.42 (q, 2H), 7.01 (dd, 1 H), 7.70 - 7.75 (m, 2H), 7.95 - 8.06 (m, 5H), 8.35 (s, 1 H), 8.53 (dd, 1 H), 9.18 (t, 1 H), 9.30 (s, 1 H).

Reference： [1]Patent: WO2011/64328,2011,A1 .Location in patent: Page/Page column 131

12
[ 57883-25-7 ]
[ 1445862-54-3 ]