17282-03-0|3-Bromo-2-chloro-5-methylpyridine| Ambeed

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Quality Control of [ 17282-03-0 ] Purity: 98% SDS Specification

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Product Details of [ 17282-03-0 ]

CAS No. :	17282-03-0
Formula :	C₆H₅BrClN
M.W :	206.47
SMILES Code :	CC1=CN=C(Cl)C(Br)=C1
MDL No. :	MFCD01830664
InChI Key :	ISNRJFOYJNIKTN-UHFFFAOYSA-N
Pubchem ID :	285437

Safety of [ 17282-03-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Computational Chemistry of [ 17282-03-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.17
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	41.91
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.13
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	2.87
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.81
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.	2.18
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	3.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.62

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.42
Solubility	0.0782 mg/ml ; 0.000379 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.	-2.8
Solubility	0.327 mg/ml ; 0.00158 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	-3.89
Solubility	0.0268 mg/ml ; 0.00013 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.	-5.52 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	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<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)	1.7

Application In Synthesis of [ 17282-03-0 ]

* 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 [ 17282-03-0 ]

[ 17282-03-0 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
		(b) Preparation of 3-bromo-2-chloro-5-methylpyridine The product from (a) (145 g) was dissolved in concentrated hydrochloric acid (750 ml) and water (450 ml) and the solution cooled to -10 C. Sodium nitrite (54 g) in cold water (450 ml) was added dropwise with stirring over a period of 90 minutes while the mixture was kept at 5 C. The solution was stirred for a further 2 hours, and then basified with concentrated ammonia, keeping the temperature below 20 C. The solid which separated was washed with water, dried, dissolved in ether (1500 ml) and washed with cold sodium hydroxide solution (1 M; 1 liter). The ether solution was washed twice with water (1 liter portions), dried, and evaporated to give the required 3-bromo-2-chloro-5-methylpyridine.
		(b) Preparation of 3-bromo-2-chloro-5-methylpyridine The product from (a) (145 g) was dissolved in concentrated hydrochloric acid (750 ml) and water (450 ml) and the solution cooled to -10 C. Sodium nitrite (54 g) in cold water (450 ml) was added dropwise with stirring over a period of 90 minutes while the mixture was kept at -5 C. The solution was stirred for a further 2 hours, and then basified with concentrated ammonia, keeping the temperature below 20 C. The solid which separated was washed with water, dried, dissolved in ether (1500 ml) and washed with cold sodium hydroxide solution (1 M; 1 liter). The ether solution was washed twice with water (1 liter portions), dried, and evaporated to give the required 3-bromo-2-chloro-5-methylpyridine.
		(b) Preparation of 3-bromo-2-chloro-5-methylpyridine The product from (a) (145 g) was dissolved in concentrated hydrochloric acid (750 ml) and water (450 ml) and the solution cooled to -10 C. Sodium nitrite (54 g) in cold water (450 ml) was added dropwise with stirring over a period of 90 minutes while the mixture was kept at -5 C. The solution was stirred for a further 2 hours, and then basified with concentrated ammonia, keeping the temperature below 20 C. The solid which separated was washed with water, dried, dissolved in ether (1500 ml) and washed with cold sodium hydroxide solution (1 M; 1 liter). The ether solution was washed twice with water (1 liter portions), dried, and evaporated to give the required 3-bromo-2-chloro-5-methylpyridine.

2
[ 17282-00-7 ]
[ 17282-03-0 ]

Yield	Reaction Conditions	Operation in experiment
		b)3-Bromo-2-chloro-5-methyl-pyridineTo a solution of 3-bromo-5-methyl-2-pyridinamuie (Example 64 (a)) (1.0 g) in a mixtureof concentrated hydrochloric acid (5 mL) and water (3 mL) at 0C was added a solution ofsodium nitrite (0.36 g) in water (3 mL). After the addition was complete, the reactionmixture was neutralised by the addition of 0.880 ammonia and the resulting precipitatecollected by filtration and purified by chromatography (SiOa, dichloromethane as eluant) togive the sub-title compound as a solid (0.47 g)MS: APCI(+ve) 206 (M+H+).

References: [1]Patent: WO2006/25783,2006,A1 .Location in patent: Page/Page column 144.

3
[ 17282-03-0 ]
[ 1018782-87-0 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride dispersion in oil (70%, 0.68 g) was added in portions to a well stirred solution of phenol (1.33 g, 14 mmol) in DMA (100 mL). After stirring the mixture for 1 h at 50 C. <strong>[17282-03-0]3-bromo-2-chloro-5-methyl-pyridine</strong> (2.68 g, 13 mmol) was added and stirring continued for 28 h at 100 C. The cooled mixture was poured into water and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1) to yield 1.4 g of the title compound as a colorless oil, 1H NMR (CDCl3): delta=2.27 (s, 3H), 7.12 (d, 2H), 7.19 (t, 1H), 7.39 (t, 2H), 7.76 (s, 1H), 7.88 (s, 1H).

References: [1]Patent: US2008/85906,2008,A1 .Location in patent: Page/Page column 31.

4
[ 17282-02-9 ]
[ 17282-03-0 ]

References: [1]Patent: US2008/85906,2008,A1 .Location in patent: Page/Page column 15.

5
[ 17282-02-9 ]
[ 17282-03-0 ]

Yield	Reaction Conditions	Operation in experiment
		3-Bromo-2-chloro-5-methyl-pyridine A mixture of 3-bromo-5-methyl-2(1H)-pyridinone (25 g, 0.13 mol) and phosphorus oxychloride (500 mL) was boiled with stirring for 20 h. Phosphorus oxychloride was removed by distillation and the residue was poured onto ice/water (800 mL). The mixture was adjusted to pH 8.5 with 2 N sodium hydroxide solution and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue, 23.4 g of the title compound as a greyish solid was introduced into the next step without purification, MS (EI) 204.9, 206.9 (M)+.
	With trichlorophosphate; for 20h;Heating / reflux;	A mixture of 3-bromo-5-methyl-2(1H)-pyridinone (25 g, 0.13 mol) and phosphorus oxychloride (500 mL) was boiled with stirring for 20 h. Phosphorus oxychloride was removed by distillation and the residue was poured onto ice/water (800 mL). The mixture was adjusted to pH 8.5 with 2 N sodium hydroxide solution and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue, 23.4 g of the title compound as a greyish solid was introduced into the next step without purification, MS (EI) 204.9, 206.9 (M)+.

References: [1]Patent: US2006/229326,2006,A1 .Location in patent: Page/Page column 20.
[2]Patent: US2008/85906,2008,A1 .Location in patent: Page/Page column 29.

6
[ 17282-03-0 ]
[ 912454-29-6 ]

Yield	Reaction Conditions	Operation in experiment
		3-Bromo-2-butoxy-5-methyl-pyridine Sodium hydride dispersion in oil (55-65%, 1.16 g) was added in portions to a well stirred solution of 1-butanol (2.4 mL, 27 mmol) in DMF (50 mL). After stirring the mixture for 1 h at room temperature <strong>[17282-03-0]3-bromo-2-chloro-5-methyl-pyridine</strong> (5.0 g, 24 mmol) was added and stirring continued for 18 h at room temperature and for 4 h at 70 C. The cooled mixture was poured into saturated sodium bicarbonate solution and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1) to yield 4.2 g of the title compound as a light red oil, MS (EI) 243.1, 245.1 (M)+.
		Sodium hydride dispersion in oil (55-65%, 1.16 g) was added in portions to a well stirred solution of 1-butanol (2.4 mL, 27 mmol) in DMF (50 mL). After stirring the mixture for 1 h at room temperature <strong>[17282-03-0]3-bromo-2-chloro-5-methyl-pyridine</strong> (5.0 g, 24 mmol) was added and stirring continued for 18 h at room temperature and for 4 h at 70 C. The cooled mixture was poured into saturated sodium bicarbonate solution and extracted with diethyl ether. Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue was purified by column chromatography on silica (n-heptane/ethyl acetate 8:1) to yield 4.2 g of the title compound as a light red oil, MS (EI) 243.1, 245.1 (M)+.

References: [1]Patent: US2006/229326,2006,A1 .Location in patent: Page/Page column 20.
[2]Patent: US2008/85906,2008,A1 .Location in patent: Page/Page column 29.

7
[ 17282-03-0 ]
[ 29241-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; In water;	(a) Preparation of 3-bromo-2-chloro-5-pyridine carboxylic acid 3-Bromo-2-chloro-5-methylpyridine (30 g) in water (650 ml) containing potassium permanganate (60 g) was stirred and heated under reflux for 3 hours. Further potassium permanganate (20 g) was then added and the mixture heated and stirred for another 21/2 hours. The mixture was steam-distilled to remove unchanged starting material, and then filtered while hot. The residue was washed with hot water. The filtrate and washings were cooled and acidified with concentrated hydrochloric acid. The solid which separated was extracted with ether. The ether extract was dried and evaporated to give 3-bromo-2-chloropyridine-5-carboxylic acid.

References: [1]Patent: US4317913,1982,A .
[2]Patent: US2008/85906,2008,A1 .Location in patent: Page/Page column 16.

8
[ 17282-03-0 ]
[ 1311148-69-2 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.

9
[ 17282-03-0 ]
[ 1311148-82-9 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.

10
[ 17282-03-0 ]
[ 1311148-92-1 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.

11
[ 17282-03-0 ]
[ 1311148-99-8 ]

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.

12
[ 17282-03-0 ]
[ 1003859-11-7 ]

Yield	Reaction Conditions	Operation in experiment
34%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 24h;Reflux;	Example 143A 3-bromo-5-(bromomethyl)-2-chloropyridine 3-Bromo-2-chloro-5-methylpyridine (4 g, 19.37 mmol), N-bromosuccinimide (3.79 g, 21.3 mmol) and benzoic peroxyanhydride (0.239 g, 0.969 mmol) were combined in carbon tetrachloride (40 mL), heated under reflux for 24 hours, cooled, and filtered to remove succinimide. The filtrate was concentrated. The resulting residue was purified by chromatography (silica gel, 0-30% ethyl acetate in heptanes) to afford the title compound (1.9 g, 34%).

References: [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 559 - 564.
[2]Patent: US2014/275026,2014,A1 .Location in patent: Paragraph 1180.

13
[ 17282-03-0 ]
[ 1219936-56-7 ]

References: [1]Patent: WO2013/111105,2013,A1 .
[2]Patent: US2013/317024,2013,A1 .

14
[ 17282-03-0 ]
[ 1219936-53-4 ]

References: [1]Patent: WO2013/111105,2013,A1 .
[2]Patent: US2013/317024,2013,A1 .

15
[ 17282-03-0 ]
[ 124-41-4 ]
[ 717843-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 65℃; for 32h;Inert atmosphere;	Step 131.4: 3-Bromo-2-methoxy-5-methyl-pyridine To a solution of <strong>[17282-03-0]3-bromo-2-chloro-5-methylpyridine</strong> (5 g, 24.2 mmol) in MeOH (80 mL) was added a solution of sodium methoxide 5.4M in MeOH (25 mL, 135 mmol) and the mixture was stirred at 65C for 32 h. The resulting suspension was filtered and the mother liquor was concentrated. Et20 and H20 were added and the phases were separated. The organic layer was washed with H20 and brine, dried (MgS04), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 90: 10? 0:100) to afford the title compound. tR: 1.03 min (LC-MS 2).
	In methanol; at 65℃; for 32h;	Step AM3: 3-Bromo-2-methoxy-5-methyl-pyridine To a solution of <strong>[17282-03-0]3-bromo-2-chloro-5-methylpyridine</strong> [17282-03-0] (5 g, 24.2 mmol) in MeOH (80 mL) was added a solution of sodium methoxide (5.4M in MeOH) (25 mL, 135 mmol) and the mixture was stirred at 65 C. for 32 h. The resulting suspension was filtered and the mother liquor was concentrated. Et2O and H2O were added and the phases were separated. The organic layer was washed with H2O and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (heptane/EtOAc: 90:10?0:100) to afford the title compound. tR: 1.03 min (LC-MS 1).

References: [1]Patent: WO2013/111105,2013,A1 .Location in patent: Page/Page column 242; 243.
[2]Patent: US2013/317024,2013,A1 .Location in patent: Paragraph 0839; 0840.

16
[ 17282-03-0 ]
[ 1219936-57-8 ]

References: [1]Patent: US2013/317024,2013,A1 .

17
[ 17282-03-0 ]
[ 1227499-44-6 ]

References: [1]Patent: US2013/317024,2013,A1 .

18
[ 17282-03-0 ]
[ 2516-33-8 ]
[ 1493777-16-4 ]