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Structure of 164513-38-6

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Quality Control of [ 164513-38-6 ] Purity: 95% SDS Specification

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Product Details of [ 164513-38-6 ]

CAS No. :	164513-38-6
Formula :	C₆H₆BrNO
M.W :	188.02
SMILES Code :	CC1=CC(O)=NC=C1Br
English Name :	5-Bromo-2-hydroxy-4-methylpyridine
MDL No. :	MFCD03427664
InChI Key :	BYGNXKDNIFHZHQ-UHFFFAOYSA-N
Pubchem ID :	819937

Safety of [ 164513-38-6 ]

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Computational Chemistry of [ 164513-38-6 ] 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	2.0
Num. H-bond donors	1.0
Molar Refractivity	38.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.77
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	1.89
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.86
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.	1.33
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	2.02
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.77

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.69
Solubility	0.384 mg/ml ; 0.00204 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.	-2.21
Solubility	1.16 mg/ml ; 0.00619 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	-2.69
Solubility	0.383 mg/ml ; 0.00204 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	No
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.	-6.11 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	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)	1.52

Application In Synthesis of [ 164513-38-6 ]

* 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 [ 164513-38-6 ]

[ 164513-38-6 ] Synthesis Path-Downstream 1~60

1
[ 98198-48-2 ]
[ 164513-38-6 ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium nitrite; In sulfuric acid; water;	a 3-Bromo-6-hydroxy-4-methyl pyridine Sodium nitrite (5.44 g, 78.8 mmol) in water (14 ml) was added dropwise to 2-amino-5-bromo-4-methylpyridine (12.83 g, 68.6 mmol) in sulphuric acid (20%) (69 ml) at 0-5 C. After 1 h at 0 C. the solution was heated to reflux for 1 h. The solution was basified to pH 10 with sodium hydroxide solution (40%) and cooled to 5 C. and the precipitated product separated by filtration. Recrystallisation from ethanol gave the title compound (5.97 g, 31%) as white needles (m.p.200-201 C.); δH (D6 -DMSO) 2.17 (3H, s, CH3), 6.40 (1H, s, 3-H), 7.76 (1H, s, 6-H), 11.58 (1H, s, NH): m/z (E.I.) 189 (M+, 100%), 187 (M+, 97%); (Found: M+, 186.9634. C6 H6 NOBr requires M, 186.9633).

References: [1]Patent: US5536745,1996,A .
[2]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

2
[ 164513-38-6 ]
[ 74-88-4 ]
[ 164513-39-7 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

3
[ 13466-41-6 ]
[ 89581-53-3 ]
[ 164513-38-6 ]
[ 18368-59-7 ]

References: [1]Synlett,2003,p. 1678 - 1682.

4
[ 164513-38-6 ]
[ 163914-13-4 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

5
[ 164513-38-6 ]
6-[2-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3S)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-1-methyl-eth-(E)-ylidene]-3-methoxy-5,6-dihydro-[2]pyrindin-7-one [ No CAS ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

6
[ 164513-38-6 ]
[ 163914-05-4 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

7
[ 164513-38-6 ]
[ 163914-00-9 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

8
[ 164513-38-6 ]
[ 163913-95-9 ]

References: [1]Tetrahedron Letters,1994,vol. 35,p. 3771 - 3774.

9
[ 164513-38-6 ]
[ 17689-66-6 ]
[ 955930-01-5 ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 35 In an atmosphere of nitrogen, sodium hydride was added under ice-cooling to a mixture of <strong>[164513-38-6]5-bromo-4-methylpyridin-2-ol</strong> and DMF, followed by stirring at room temperature for 1 hour. Then, 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate was added thereto, followed by stirring at 40C for 14 hours to obtain 4-[(5-bromo-4-methylpyridin-2-yl)oxy]2-methylbutan-2-ol and 5-bromo-1-(3-hydroxy-3-methylbutyl)-4-methylpyridin-2(1H)-one.
		<Step 2> Synthesis of 4-(5-bromo-4-methylpyridin-2-yloxy)-2-methylbutan-2-ol To a suspension of sodium hydride (to which about 40% of a mineral oil was added, 0.23 g) in N,N-dimethylformamide (10 mL), <strong>[164513-38-6]5-bromo-2-hydroxy-4-methylpyridine</strong> (1.00 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, 3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate (1.51 g) was added and the resultant reaction mixture was stirred at 60 C. for 4 hours. To the reaction mixture, a aqueous solution of saturated ammonium chloride was added and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67) to obtain the subject compound (0.92 g) as a light yellow oil.
		<Step 2> Synthesis of 4-(5-bromo-4-methylpyridin-2-yloxy)-2-methylbutan-2-ol To a suspension of sodium hydride (to which about 40% of a mineral oil was added, 0.23 g) in N,N-dimethylformamide (10 mL), <strong>[164513-38-6]5-bromo-2-hydroxy-4-methylpyridine</strong> (1.00 g) was added under ice-cooling and the resultant reaction mixture was stirred for 30 minutes. To the reaction mixture, 3-hydroxy-3-methylbutyl 4-methylbenzene sulfonate (1.51 g) was added and the resultant reaction mixture was stirred at 60 C. for 4 hours. To the reaction mixture, a saturated ammonium chloride aqueous solution was added and the resultant reaction mixture was extracted with ethyl acetate. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=50:50 to 33:67) to obtain the subject compound (0.92 g) as a pale yellow oil.

References: [1]Patent: EP2011788,2009,A1 .Location in patent: Page/Page column 23.
[2]Patent: US2012/157459,2012,A1 .Location in patent: Page/Page column 60.
[3]Patent: US2012/220772,2012,A1 .Location in patent: Page/Page column 66.

10
[ 75-45-6 ]
[ 164513-38-6 ]
[ 1079352-13-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water; at 70℃;	5N aqueous solution of sodium hydroxide (5.70 mL) was added to the tetrahydrofuran solution (28 mL) of <strong>[164513-38-6]5-bromo-2-hydroxy-4-methylpyridine</strong> (1.07 g). The reaction mixture was stirred at 70C under chlorodifluoromethane gas atmosphere. The reaction mixture was cooled to room temperature after the disappearance of raw material, diluted with tert-butyl methyl ether, and extracted. The organic layer was washed by water and a saturated aqueous solution of sodium chloride, and dried with magnesium sulfate. The organic layer was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (high flash-SI, size L (made in Yamazen corporation)) to obtain a title compound (751 mg) having the following physical data. TLC:Rf 0.58 (ethyl acetate/n-hexane=5/95); 1H-NMR(CDCl3): δ 2.40 (d, J=0.7 Hz, 3 H), 6.80 (s, 1 H), 7.39 (t, J=72.9 Hz, 1 H), 8.22 (s, 1 H).

References: [1]Patent: EP2154139,2010,A1 .Location in patent: Page/Page column 38.

11
[ 164513-38-6 ]
[ 778611-64-6 ]

References: [1]Molecules,2012,vol. 17,p. 4533 - 4544.

12
[ 88157-42-0 ]
[ 164513-38-6 ]
[ 1383001-33-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 70℃; for 4h;	Example 100[0357] [Formula 129][0358] 1) In tetrahydrofuran (26 mL) was dissolved <strong>[164513-38-6]5-bromo-4-methylpyridin-2-ol</strong> (1.3 g), methyl l-(hydroxymethyl)cyclopropanecarboxylate (1.08 g) and triphenylphosphine (2.72 g), and 40% diethyl azodicarboxylate-toluene solution (4.72 mL) was added dropwise to the solution at 0C. The mixture was stirred at 70C for 4 hours. The reaction mixture was cooled to room temperature, water and ethyl acetate were added to the mixture, and the organic layer was washed with a saturated brine and dried over anhydrous sodium sulfate. After concentrating the mixture under reduced pressure, the obtained residue was purified by silica gel column chromatography (n-hexane: ethyl acetate=99: l to 99:5) to obtain methyl l-[(5-bromo-4-methylpyridin-2-yl)oxy]- methyljcyclopropanecarboxylate (2.08 g).MS (m/z): 300/302 [M+H]+

References: [1]Patent: WO2012/81736,2012,A1 .Location in patent: Page/Page column 105-106.

13
[ 1195-81-9 ]
[ 164513-38-6 ]
[ 1383001-19-1 ]