866755-20-6|2,6-Dichloro-3-bromopyridine| Ambeed

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Quality Control of [ 866755-20-6 ] Purity: 98% SDS Specification

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Product Details of [ 866755-20-6 ]

CAS No. :	866755-20-6
Formula :	C₅H₂BrCl₂N
M.W :	226.89
SMILES Code :	BrC1=CC=C(N=C1Cl)Cl
MDL No. :	MFCD06798231
InChI Key :	PZHASTRIYXMWKM-UHFFFAOYSA-N
Pubchem ID :	21551819

Safety of [ 866755-20-6 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H315-H318-H335
Precautionary Statements:	P261-P280-P301+P310-P305+P351+P338
Class:	8(6.1)
UN#:	2923
Packing Group:	Ⅲ

Computational Chemistry of [ 866755-20-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	41.96
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.	2.1
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	2.83
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.15
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.	2.44
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	3.39
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.78

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.52
Solubility	0.0681 mg/ml ; 0.0003 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.	-2.76
Solubility	0.396 mg/ml ; 0.00174 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	-4.12
Solubility	0.0174 mg/ml ; 0.0000766 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.67 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)	1.74

Application In Synthesis of [ 866755-20-6 ]

* 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 [ 866755-20-6 ]

[ 866755-20-6 ] Synthesis Path-Downstream 1~35

Yield	Reaction Conditions	Operation in experiment
		Representative halopyridine compounds which can be prepared by the method of the present invention include: ... 2,5,6-trifluoropyridine; 2,5-dichloro-6-fluoropyridine; 2,5-dichloro-6-bromopyridine; 2,6-dichloro-5-fluoropyridine; 2,6-dichloro-5-bromopyridine; 2,6-difluoro-5-chloropyridine; 2,6-dibromo-5-chloropyridine and 2,6-difluoro-5-bromopyridine.

2
[ 866755-20-6 ]
[ 389890-43-1 ]
[ 1349184-97-9 ]

Yield	Reaction Conditions	Operation in experiment
56%	With caesium carbonate; In acetonitrile; at 20.0℃;	To a mixture of <strong>[866755-20-6]3-bromo-2,6-dichloropyridine</strong> (4.5 g, 20 mmol ) and tert-butyl ((l S,3S)-3-hydroxycyclobutyl)carbamate (see PREPARATION 4A; 3.65 g, 20 mmol) in acetonitrile (50 mL) was added CS2CO (13.2 g, 40 mmol), and then the mixture was stirred at RT overnight. The reaction mixture was filtered and concentrated under vacuum to give tert- butyl ((l S,3S)-3-((3-bromo-6-chloropyridin-2-yl)oxy)cyclobutyl)carbamate (4.2 g, 11.2 mmol, 56%). ESI-MS (M+1): 377 calc. for Ci4Hi8BrClN203 376.

References: [1]Patent: WO2011/143366,2011,A1 .Location in patent: Page/Page column 66.

3
[ 109-01-3 ]
[ 866755-20-6 ]
[ 1418153-18-0 ]
[ 1418153-33-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 6940 - 6952.

4
[ 866755-20-6 ]
[ 80392-79-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With cesium fluoride; In dimethyl sulfoxide; at 80.0℃; for 8.0h;	General procedure: To asolution of <strong>[866755-20-6]3-bromo-2,6-dichloropyridine</strong> (4.70 g, 20.7 mmol) in DMSO (103 ml)was added cesium fluoride (12.6 g, 82.9 mmol) at room temperature. The mixturewas stirred at 80 C under air for 8 h. The mixture was poured into water atroom temperature and extracted with Et2O. The organic layer wasseparated, washed with water and brine, dried over Na2SO4and concentrated in vacuo. (400 Torr, 40 C). The residue was purified bycolumn chromatography (silica gel, eluted with EtOAc in hexane) to give 3-bromo-2,6-difluoropyridine (3B) (2.58 g, 64%) as colorless oil. 1H NMR (CDCl3)delta: 6.79 1H,dd, J = 8.3, 3.0 Hz), 8.03 (1H, ddd, J = 8.4, 8.4 7.0 Hz). 19F NMR(CDCl3) delta: -69.3 Hz, -63.8 Hz. The compound 4B-8B were prepared in a manner similarto that described for 3B.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 6043 - 6046.

5
[ 866755-20-6 ]
N-benzyl-5-bromo-6-fluoropyridin-2-amine [ No CAS ]
N-benzyl-3-bromo-6-fluoropyridin-2-amine [ No CAS ]

References: [1]Tetrahedron Letters,2015,vol. 56,p. 6043 - 6046.

6
[ 866755-20-6 ]
[ 64-17-5 ]
[ 1310416-63-7 ]
3-bromo-2-chloro-6-ethoxypyridine [ No CAS ]
3-bromo-6-chloro-2-ethoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; at 70.0℃;	Fresh cut sodium (0.101 g 4.41 mmol) was added to EtOH (50 mL) . The resulting mixture was stirred at rt. After the solid dissolved 3-bromo-2 6-dichloropyridine (1 g 4.41 mmol) was added. The resulting mixture was stirred at 70 overnight. After LCMS analysis showed the starting material was disappeared. The solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with H2O (20 mL) and brine (20 mL) . The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica column chromatography (PE/EA 20/1) to yield a white solid of a mixture of 3-bromo-2-chloro-6-ethoxypyridine 3-bromo-2 6-diethoxypyridine and 3-bromo-6-chloro-2-ethoxypyridine (930 mg 3.85 mmol 87yield) 1HNMR(400 MHz CD3OD) delta 7.85 (d J 1.2 Hz 1H) 6.88 (d J 8.0 Hz 1H) 4.42-4.36 (m 2H) 1.39 (t J 7.2 Hz 3H) ES-LCMS m/z 235.9 237.9 (M+H)

References: [1]Patent: WO2016/37578,2016,A1 .Location in patent: Page/Page column 183.

7
[ 866755-20-6 ]
3-bromo-2-ethoxy-6-((4-methoxybenzyl)oxy)pyridine [ No CAS ]

References: [1]Patent: WO2016/37578,2016,A1 .

8
[ 866755-20-6 ]
1-(4-(2-ethoxy-6-((4-methoxybenzyl)oxy)pyridin-3-yl)-2-fluorophenyl)-3-(4-((3-methyloxetan-3-yl)oxy)-3-(trifluoromethyl)phenyl)urea [ No CAS ]

References: [1]Patent: WO2016/37578,2016,A1 .

9
[ 866755-20-6 ]
1-(4-(2-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-3-(4-((3-methyloxetan-3-yl)oxy)-3-(trifluoromethyl)phenyl)urea [ No CAS ]

References: [1]Patent: WO2016/37578,2016,A1 .

10
[ 866755-20-6 ]
C₉H₁₂BrN₃O [ No CAS ]

References: [1]Patent: WO2017/46318,2017,A1 .

11
[ 866755-20-6 ]
C₁₀H₁₀BrN₃O₂ [ No CAS ]

References: [1]Patent: WO2017/46318,2017,A1 .

12
[ 866755-20-6 ]
5-(cyclopropylmethoxy)-6-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]

References: [1]Patent: WO2017/46318,2017,A1 .

13
[ 866755-20-6 ]
[ 2516-33-8 ]
C₉H₉BrClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With caesium carbonate; In acetonitrile; at 80.0℃;	3-Bromo-2,6-dichloropyridine (1.04 g, 4.58 mmol), cyclopropylmethanol (1.6 g, 22.91 mmol)and Cs2C03 (2.9 g, 9.16 mmol) were added to CH3CN (40 ml). This reaction mixture wasstirred overnight at 80 C. The mixture was filtered and concentrated in vacuo to affordCAP-004-32-1 (1.05 g, 80 %) as a brown oil, which was used to the next step withoutfurther purification.

References: [1]Patent: WO2017/46318,2017,A1 .Location in patent: Page/Page column 56.

14
[ 866755-20-6 ]
[ 62-53-3 ]
3-bromo-6-chloro-N-phenylpyridin-2-amine [ No CAS ]
5-bromo-6-chloro-N-phenylpyridin-2-amine [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 10613 - 10616.

15
[ 866755-20-6 ]
N-(2-fluoro-6-methoxybenzyl)-8-(5-methyl-1,3,4-oxadiazol-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-5-amine [ No CAS ]