[ CAS No. 126325-46-0 ] {[proInfo.proName]}

Name: 126325-46-0|2-Amino-3-bromo-6-methylpyridine|98%
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Quality Control of [ 126325-46-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 126325-46-0 ]

Product Details of [ 126325-46-0 ]

CAS No. :	126325-46-0	MDL No. :	MFCD03095215
Formula :	C₆H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JYWWGZAAXTYNRN-UHFFFAOYSA-N
M.W :	187.04	Pubchem ID :	2734416
Synonyms :

Calculated chemistry of [ 126325-46-0 ]

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 :	1.0
Molar Refractivity :	41.31
TPSA :	38.91 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) :	-6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.89
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	1.78
Consensus Log Po/w :	1.67

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.5
Solubility :	0.59 mg/ml ; 0.00316 mol/l
Class :	Soluble
Log S (Ali) :	-2.03
Solubility :	1.75 mg/ml ; 0.00936 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.91
Solubility :	0.232 mg/ml ; 0.00124 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 126325-46-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 126325-46-0 ]

* 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.

Upstream synthesis route of [ 126325-46-0 ]
Downstream synthetic route of [ 126325-46-0 ]

[ 126325-46-0 ] Synthesis Path-Upstream 1~5

1
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374

2
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374

3
[ 1824-81-3 ]
[ 126325-46-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sulfuric acid; bromine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water	Step 1 Preparation of 6-amino-5-bromo-picoline 32.4 g (0.3 mole) of 6-aminopicoline was dissolved in a mixture of 28 g of conc. sulfuric acid and 120 ml of water and the resulting solution was cooled in ice water. 52.8 g (0.33 mole) of bromine was added dropwise to the solution over 30 minutes at 0° C. The reaction solution was stirred for 20 minutes at room temperature and neutralized with cold aqueous NaOH solution. The resultant was filtered and the solid was purified with column chromatography using methylene chloride and ethyl acetate as an eluent to obtain 31 g of the title compound (yield 55percent).

Reference： [1] Patent: US5691348, 1997, A,

4
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[2] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374

5
[ 126325-46-0 ]
[ 178876-82-9 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 6, p. 650 - 654

[ 126325-46-0 ] Synthesis Path-Downstream 1~46

1
[ 1824-81-3 ]
[ 42753-71-9 ]
[ 91872-10-5 ]
[ 126325-46-0 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 369 - 374
[2]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 369 - 374

2
[ 108-24-7 ]
[ 126325-46-0 ]
[ 875051-78-8 ]

Yield	Reaction Conditions	Operation in experiment
75%		Preparation 1; N-(3-Bromo-6-methvl-pvridin-2-vn-acetamide; Acetic anhydride (21 mL, 223mmol) was added to a solution of <strong>[126325-46-0]2-amino-3-bromo-6-picoline</strong> (10g, 53.46mmol) in dioxan (50ml_) and the mixture was stirred at 50C for 18 hours. The solvent was then evaporated under reduced pressure and the residue was diluted with saturated sodium hydrogen carbonate solution (150ml_). The precipitate was filtered off, washed with water and re-dissolved in dichloromethane, and the filtrate was neutralised to pH7 with saturated sodium hydrogen carbonate solution and extracted with dichloromethane (3x100ml_). The organic solutions were combined, washed with water, dried over magnesium sulfate and concentrated in vacua to give a white solid. Purification of the solid by column chromatography on silica gel, eluting with ethyl acetateiheptane, 75:25, afforded the title compound as a white solid in 75% yield, 9.2g.
75%		Preparation 1. N-(3-Bromo-6-methyl-pyridin-2-yl)-acetamide. Acetic anhydride (21 ml_, 223 mmol) was added to a solution of <strong>[126325-46-0]2-amino-3-bromo-6-picoline</strong> (10 g, 53.46 mmol) in 1 ,4-dioxan (50 ml_) and the mixture was stirred at 5O0C for 18 hours. The solvent was then evaporated under reduced pressure and the residue was diluted with saturated sodium hydrogen carbonate solution (150 mL). The precipitate was filtered off, washed with water and re-dissolved in dichloromethane, and the filtrate was neutralised to pH7 with saturated sodium hydrogen carbonate solution and extracted with dichloromethane (3x100 mL). The organic solutions were combined, washed with water, dried sulphate(MgSO4) and concentrated in vacuo to give a white solid. Purification of the solid by column chromatography on silica gel, eluting with ethyl acetate:heptane, 75:25, afforded the title compound as a white solid in 75% yield, 9.2 g.1H NMR (400MHz, CD3OD) delta: 2.17(s, 3H), 2.49(s, 3H), 7.09(d, 1H), 7.94(d, 1H) LRMS: m/z APCI 231[MH]+Microanalysis: C8H9BrN2O requires: C 41.95; H 3.96 N 12.23; found C 41.92; H 3.91 , N 12.16

Reference： [1]Organic Process Research and Development,2010,vol. 14,p. 263 - 271
[2]Patent: WO2006/11050,2006,A2 .Location in patent: Page/Page column 45-46
[3]Patent: WO2007/83239,2007,A1 .Location in patent: Page/Page column 35
[4]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 650 - 654

3
[ 1824-81-3 ]
[ 126325-46-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sulfuric acid; bromine; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water;	Step 1 Preparation of 6-amino-5-bromo-picoline 32.4 g (0.3 mole) of 6-aminopicoline was dissolved in a mixture of 28 g of conc. sulfuric acid and 120 ml of water and the resulting solution was cooled in ice water. 52.8 g (0.33 mole) of bromine was added dropwise to the solution over 30 minutes at 0 C. The reaction solution was stirred for 20 minutes at room temperature and neutralized with cold aqueous NaOH solution. The resultant was filtered and the solid was purified with column chromatography using methylene chloride and ethyl acetate as an eluent to obtain 31 g of the title compound (yield 55%).

Reference： [1]Patent: US5691348,1997,A

4
C₂₆H₂₉ClF₄N₂O₄ [ No CAS ]
[ 126325-46-0 ]
C₃₂H₃₅BrF₄N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine;tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 110℃; for 24.0h;	Benzylchloride 3a4 (59 mg, 0.1 1 mmol) is combined with 2-amino-3-bromo-6- methylpyridine (30 mg, 0.16 mmol), TBABr (7 mg, 0.02 mmol) and DIPEA (40 mul_, 0.22 mmol) in DMF (1 ml_). The mixture is heated to 11O0C and is stirred for 1 day. Methanol (0.5 mL) is added followed by aqueous NaOH (1 N, 2 ml_, 2.0 mmol) then the mixture is stirred at RT for 73 hours. The mixture is acidified with AcOH (2 mL) then the volatiles are removed in vacuo. The residue is taken-up in AcOH (2.5 mL) then injected onto the preparative HPLC to isolate compound 1102.

Reference： [1]Patent: WO2009/18656,2009,A1 .Location in patent: Page/Page column 77

5
[ 3282-30-2 ]
[ 126325-46-0 ]
[ 135995-44-7 ]

Reference： [1]Organic Process Research and Development,2010,vol. 14,p. 263 - 271

6
[ 108-24-7 ]
[ 126325-46-0 ]
[ 875051-78-8 ]
[ 1221629-00-0 ]

Reference： [1]Organic Process Research and Development,2010,vol. 14,p. 263 - 271

7
[ 110-91-8 ]
[ 126325-46-0 ]
[ 1286273-54-8 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1984 - 1987

8
[ 40972-86-9 ]
[ 126325-46-0 ]
[ 1609373-95-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 5h;Reflux;	A solution of <strong>[126325-46-0]3-bromo-6-methylpyridin-2-amine</strong> (12.33 g, 65.9 mmol) and (2,3-dimethoxyphenyl)boronic acid(12.0 g, 65.9 mmol), Pd(PPh3)4 (2.286 g, 1.978 mmol) and sodium carbonate (6.99 g, 65.9 mmol) in DME (250 ml) andwater (125 ml) was stirred at reflux for 5 h. The crude mix was filtered through celite and the solid was washed with ethylacetate. The filtrate was washed with brine and the solvent was evaporated. The crude product was purified by columnchromatography on silica gel with 0-5% methanol in DCM as eluent to obtain 14.5 grams (90%) of the desired productas a cream colored solid.

Reference： [1]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0149; 0150

9
[ 126325-46-0 ]
[ 1609374-01-7 ]

Reference： [1]Patent: EP2730583,2014,A1

10
[ 126325-46-0 ]
[ 1609373-96-7 ]

Reference： [1]Patent: EP2730583,2014,A1

11
[ 126325-46-0 ]
[ 1609373-97-8 ]

Reference： [1]Patent: EP2730583,2014,A1

12
[ 126325-46-0 ]
[ 1609373-98-9 ]

Reference： [1]Patent: EP2730583,2014,A1

13
[ 126325-46-0 ]
[ 1609373-99-0 ]

Reference： [1]Patent: EP2730583,2014,A1

14
[ 126325-46-0 ]
[ 1609368-30-0 ]

Reference： [1]Patent: EP2730583,2014,A1

15
[ 126325-46-0 ]
[ 1609368-31-1 ]

Reference： [1]Patent: EP2730583,2014,A1

16
[ 126325-46-0 ]
[ 1609368-32-2 ]

Reference： [1]Patent: EP2730583,2014,A1

17
[ 126325-46-0 ]
[ 1609368-33-3 ]

Reference： [1]Patent: EP2730583,2014,A1

18
[ 126325-46-0 ]
[ 1609374-00-6 ]

Reference： [1]Patent: EP2730583,2014,A1

19
[ 126325-46-0 ]
C₁₂H₈Cl₃N₃O [ No CAS ]