[ CAS No. 126325-53-9 ] {[proInfo.proName]}

Name: 126325-53-9|2-Bromo-6-methylpyridin-3-amine|98%
Brand: Ambeed
SKU: A494266
Price: 5.0 USD
Availability: InStock
Rating: 93 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 126325-53-9

Structure of 126325-53-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 126325-53-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 126325-53-9 ]

SDS Specification

Alternatived Products of [ 126325-53-9 ]

Product Details of [ 126325-53-9 ]

CAS No. :	126325-53-9	MDL No. :	MFCD03095078
Formula :	C₆H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KLVZEEUNGGOROA-UHFFFAOYSA-N
M.W :	187.04	Pubchem ID :	14418051
Synonyms :

Calculated chemistry of [ 126325-53-9 ]

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) :	1.63
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.74
Log Po/w (MLOGP) :	0.92
Log Po/w (SILICOS-IT) :	1.78
Consensus Log Po/w :	1.54

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 :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.75

Safety of [ 126325-53-9 ]

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

Application In Synthesis of [ 126325-53-9 ]

* 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 [ 126325-53-9 ]
Downstream synthetic route of [ 126325-53-9 ]

[ 126325-53-9 ] Synthesis Path-Upstream 1~2

1
[ 80287-53-2 ]
[ 126325-53-9 ]

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
[ 126325-53-9 ]
[ 374633-36-0 ]

Yield	Reaction Conditions	Operation in experiment
38%	Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 0℃; Stage #2: With hexafluorophosphoric acid In waterCooling Stage #3: at 100℃; for 0.166667 h;	General procedure: 3-Amino-2-bromo-6-methylpyridine(7a) or4-amino-2-bromo-6-methylpyridine(7b) (25.20 g, 134.73 mmol) wasadded to a mixture of water (78.1 mL) and conc. HCl (12.8 mL, 350.30 mmol), andthen the mixture was cooled to 0 ^oC. To it, sodium nitrite (18.6 g,269.46 mmol) was added portionwise with stirring over a period of 20 min whilekeeping the reaction temperature between –5 ^oCand 0 ^oC. After 10 min, 65percent hexafluorophosphoric acidsolution (43.26 g, 296.41 mmol) was added dropwise with cooling, atwhich point a lot of precipitates were formed. The precipitates were collectedby filteration using a glass filter funnel, washed with cold water (2 × 50 mL) and diethyl ether (100 mL), and then dried in the air for 48 h.The solid was slowly heated to 100 ^oC (very exothermic), and a darkred oily material was formed after 10 min. The oil was basified with dilutedNaOH solution to pH~10 and extracted with CH₂Cl₂ (2 × 150 mL). The combined organic layer was dried over anhydrous Na₂SO₄,filtered, and evaporated to dryness under reduced pressure. The residue waspurified by MPLC on neutral alumina using hexane/EtOAc (10:1) as eluent to affordthe titled compounds.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5228 - 5231

[ 126325-53-9 ] Synthesis Path-Downstream 1~46

1
[ 80287-53-2 ]
[ 126325-53-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; In dichloromethane; at 0℃; for 1.5h;Inert atmosphere;	Compound 308 6-methylpyridin-3-amine 37a (10.8 g, 100 mmol) was dissolved in 20 dichloromethane (500 mL) and cooled to 0 C. 14 N-Bromosuccinimide (17.8 g, 100 mmol) was added slowly within 1 h. Then the reaction mixture was stirred at 0 C. for 30 min. The mixture was washed with saturated aqueous sodium bicarbonate solution (200 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the target 309 product 2-bromo-6-methylpyridin-3-amine 37b (17.3 g, light brown solid). Yield: 93%. MS m/z (ESI): 187/189[M+1]

Reference： [1]Patent: US2019/185472,2019,A1 .Location in patent: Paragraph 0246; 0600-0603
[2]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 369 - 374
[3]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 369 - 374

2
[ 126325-53-9 ]
[ 2365-48-2 ]
[ 132872-41-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1990,vol. 332,p. 444 - 452

3
[ 126325-53-9 ]
[ 536-74-3 ]
[ 757950-00-8 ]

Yield	Reaction Conditions	Operation in experiment
47%	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; for 14h;Heating / reflux;	To a solution of Cul (10 mg, 50 P, MOT) in triethylamine (5 ml) were added (2-bromo-6- methyl-pyridin-3-yl) amine (200 mg, 1.07 MMOL) and (PPh3) 2PDCI2 (36 mg, 50 PMOL). The reaction mixture was cooled to 0C and PHENYLACETYLENE (176 PI, 1.60 MMOL) was added. The reaction mixture was allowed to warm to room temperature and then heated under reflux for 14 h. The solvent was evaporated and the crude residue was purified by flash chromatography (HEXANE/ETHYL acetate 4: 1) to yield 105 mg (0.50 mmol, 47%) of (6-methyl-2-phenylethynyl-pyridin-3-yl) amine as a yellow solid. Rf: 0.09 (HEXANE/ETHYL acetate 4: 1). M. p.: 154-155C. H NMR (CDCI3, 400 MHz) 6 : 2.47 (s, 3 H), 4.13-4. 17 (br. s, 2 H), 6.93-7. 01 (2 H), 7.34-7. 39 (3 H), 7.57-7. 63 (2 H). (6-METHYL-2-PHENYLETHYNYL-PYRIDIN-3-YL) amine (105 mg, 0.50 mmol) was dissolved in CHCl3 (2 ml) and treated with 1. 56 ml (1. 25 MMOL) of 0. 8 M hydrochloric acid solution in diethyl ether. After evaporation of the solvent and trituration of the residue with ethyl acetate, 107 mg (0.44 mmol, 87%) of the title hydrochloride were obtained as a yellowish solid.

Reference： [1]Patent: WO2004/78728,2004,A1 .Location in patent: Page 12

4
[ 126325-53-9 ]
[ 191327-30-7 ]
C₁₈H₁₄BrClN₂O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 409 - 413

5
[ 1227409-84-8 ]
[ 126325-53-9 ]
[ 1227409-85-9 ]

Yield	Reaction Conditions	Operation in experiment
9.4%	With potassium carbonate; 1,4-di(diphenylphosphino)-butane;palladium diacetate; In acetonitrile; at 80℃; for 15h;Inert atmosphere;	Paradium acetate (19 mg, 0.027 mmol) was added to acetonitril solution (5.0 mL) of the intermediate 19 (308 mg, 1.18 mmol), <strong>[126325-53-9]3-amino-2-bromo-6-methylpyridine</strong> (200 mg, 107 mmol), 1,4-bis(diphenylphosphino)butane (dppb) (18.3 mg, 0.043 mmol) and Potassium carbonate (444 mg, 3.21 mmol) under the nitrogen atmosphere. The resulting mixture was stirred at 80 C. for 15 hours. After that, the resulting mixture was filtered through celite, and the obtained filtrate was concentrated under reduced pressure. The residue was purified with column chromatography (dichloromethanee/methanol=25/1-10/1(v/v)) using silicagel to afford the intermediate 20 (36.9 mg, 9.4% yield) as a dark-yellow crystal.1H-NMR (300 MHz, CDCl3) delta 7.28-7.18 (br s, 1H), 7.03-6.98 (m, 3H), 4.14 (br s, 2H), 4.04 (s, 3H), 3.78-3.71 (m, 4H), 3.59-3.50 (m, 2H), 2.63-2.45 (m, 6H), 2.47 (s, 3H).MS (ESI)m/z; [M+H]+369.

Reference： [1]Patent: US2011/275628,2011,A1 .Location in patent: Page/Page column 27

6
[ 126325-53-9 ]
[ 98-80-6 ]
[ 1610529-35-5 ]

Reference： [1]Patent: WO2014/78408,2014,A1

7
[ 126325-53-9 ]
[ 98-80-6 ]
[ 1214387-73-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 95℃; for 16h;Sealed tube;	Intermediate 29 phenyl (6-methvI-2-phenylpyridin-3 -vDcarbamate [00471] Step A: Preparation of 6-methyl-2-phenylpyridin-3-amine: Phenyl boronic acid (424 mg, 3.48 mmol), K2C03 (1.48 g, 10.7 mmol) and Pd(PPh3)4 (309 mg, 0.27 mmol) were combined in toluene (6 mL), water (3 mL) and EtOH (1.5 mL) then treated with 2-bromo-6- methylpyridin-3 -amine (500 mg, 2.67 mmol). The mixture was warmed to 95 C in a sealed tube for 16 hours then cooled and partitioned between EtOAc (30 mL) and saturated NH4C1 (30 mL). The aqueous layer was extracted with EtOAc (2 x 30 mL) and the combined organic phases were washed with brine (30 mL), dried over Na2S04, filtered and concentrated under vacuum. The residue was purified by silica column chromatography eluting with 4:1 hexanes / EtOAc to afford 6-methyl-2-phenylpyridin-3-amine (407 mg, 83% yield) as a pale yellow crystalline solid. MS (apci) m/z = 185.1 (M+H).

Reference： [1]Patent: WO2014/78408,2014,A1 .Location in patent: Paragraph 00471

8
tert-butyl N-[(1S)-1-[3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]but-3-en-1-yl]carbamate [ No CAS ]
[ 126325-53-9 ]
tert-butyl N-[(1S)-1-[3-(3-amino-6-methylpyridin-2-yl)phenyl]but-3-en-1-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 120℃; for 0.5h;Inert atmosphere; Microwave irradiation;	tert-Butyl N- [(15)-i -[3 -(5,5 -dimethyl- 1,3 ,2-dioxaborinan-2-yl)phenyl]but-3 -en-i - yl]carbamate (0.67 g, 1.865 mmol), <strong>[126325-53-9]2-bromo-6-methylpyridin-3-amine</strong> (0.349 g, 1.865mmol), and 2 M aq Na2CO3 (4 mL, 8.00 mmol) were added to dioxane (9 ml) and the solution was purged with a stream of Ar for 10 mi Pd(PPh3)4 (0.108 g, 0.093 mmol) was added and the mixture was irradiated in a microwave at 120 C for 30 mm. The reaction was quenched with water (20 ml) and extracted with EtOAc (3 x 30 ml). The combined organic layers were washed with brine (15 ml), dried (MgSO4), filtered andconcentrated. The residue was purified by normal phase chromatography using DCM and0-10% MeOH as eluents to afford tert-butyl N- [(15)-i -[3 -(3 -amino-6-methylpyridin-2-yl)phenyl]but-3-en-1-yl]carbamate (0.94g, 100%, 70% purity) as a brown oil. MS(ESI) m/z: 354.5 (M+H).

Reference： [1]Patent: WO2015/116886,2015,A1 .Location in patent: Page/Page column 288; 289

9
[ 126325-53-9 ]
3-fluoro-6-methyl-2-pyridinecarboxaldehyde [ No CAS ]