[ CAS No. 122759-89-1 ] {[proInfo.proName]}

Name: 122759-89-1|6-Bromo-7-methylquinoline|97%
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SKU: A157848
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Quality Control of [ 122759-89-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 122759-89-1 ]

SDS Specification

Alternatived Products of [ 122759-89-1 ]

Product Details of [ 122759-89-1 ]

CAS No. :	122759-89-1	MDL No. :	MFCD18260428
Formula :	C₁₀H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NMGWSJBVVZOOST-UHFFFAOYSA-N
M.W :	222.08	Pubchem ID :	57911018
Synonyms :

Calculated chemistry of [ 122759-89-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.1
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.41
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	3.25
Log Po/w (WLOGP) :	3.31
Log Po/w (MLOGP) :	2.85
Log Po/w (SILICOS-IT) :	3.6
Consensus Log Po/w :	3.06

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.88
Solubility :	0.0292 mg/ml ; 0.000132 mol/l
Class :	Soluble
Log S (Ali) :	-3.19
Solubility :	0.142 mg/ml ; 0.000639 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.95
Solubility :	0.00251 mg/ml ; 0.0000113 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 122759-89-1 ]

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

Application In Synthesis of [ 122759-89-1 ]

* 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 [ 122759-89-1 ]
Downstream synthetic route of [ 122759-89-1 ]

[ 122759-89-1 ] Synthesis Path-Upstream 1~2

1
[ 6933-10-4 ]
[ 56-81-5 ]
[ 122759-89-1 ]

Yield	Reaction Conditions	Operation in experiment
25%	With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 120 - 130℃; for 1.5 h;	The raw materials 3,5-difluoroaniline G-1 (5.6 g, 27 mmol) and sodium 3-nitrobenzenesulfonate (7.2 g, 32 mmol) Was added to a mixed solution of concentrated sulfuric acid (15 mL) and water (6 mL) After heating to an internal temperature of 120 ° C, glycerol (7.4 g, 80 mmol) After the addition was completed, the temperature was raised to 130 ° C and reacted for 1.5h, then cooled. The reaction was poured into crushed ice, concentrated ammonia water to adjust the pH to 5 ~ 6, the precipitated solid was filtered off, washed with water, After drying, column chromatography gave 3.82 g of white solid compound G-2 in 58percent yield. A mixture of 6-bromo-7-methylquinoline (I-2) and 6-bromo-5-methylquinoline (J-1) was synthesized. Then separated by supercritical preparative chromatography (SFC), IC-H column, mobile phase: isopropanol / carbon dioxide = 18/82, detection wavelength: 254nm. The first fraction was collected as 6-bromo-7-methylquinoline (I-2) as a white solid, yield: 25percent. The second fraction was collected as a 6-bromo-5-methylquinoline (J-1) white solid in a yield of 20percent

Reference： [1] Patent: CN105968115, 2016, A, . Location in patent: Paragraph 0492; 0518-0520
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4281 - 4290

2
[ 6933-10-4 ]
[ 56-81-5 ]
[ 122759-89-1 ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: With iron(III) sulfate; sulfuric acid In nitrobenzene for 3 h; Heating / reflux Stage #2: With water; sodium hydrogencarbonate In nitrobenzene	Intermediate 4: 6-Bromo-7-methyl-quinoline; [0304] A mixture of 4-bromo-3-methylaniline (20 g, 107.5 mmol), ferric sulfate (6.6 g, 43.4 mmol), glycerol (40.8 g, 440 mmol), nitrobenzene (8.12 g, 66 mmol), and concentrated EPO <DP n="81"/>sulfuric acid (23 ml) was heated gently. After the first vigorous reaction, the mixture was boiled for 3h and then evaporated to remove the excess nitrobenzene. The solution was added a saturated aqueous solution of sodium bicarbonate until pH=7-8, then the solution was filtered and extracted with dichloromethane. The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The solid was purified by flash column chromatography to give a yellow solid, which was further washed with petroleum ether to give 7.5 g of 6-bromo-7-methyl-quinoline (31percent yield): ¹H NMR (CDCl₃): 2.60 (s, 3H), 7.36 (m, IH), 7.96 (s, IH), 8.04 (m, 2H), 8.89 (m, IH).

Reference： [1] Patent: WO2008/51808, 2008, A2, . Location in patent: Page/Page column 79-80

[ 122759-89-1 ] Synthesis Path-Downstream 1~47

1
[ 6933-10-4 ]
[ 56-81-5 ]
[ 122759-89-1 ]

Yield	Reaction Conditions	Operation in experiment
31%		Intermediate 4: 6-Bromo-7-methyl-quinoline; [0304] A mixture of 4-bromo-3-methylaniline (20 g, 107.5 mmol), ferric sulfate (6.6 g, 43.4 mmol), glycerol (40.8 g, 440 mmol), nitrobenzene (8.12 g, 66 mmol), and concentrated EPO <DP n="81"/>sulfuric acid (23 ml) was heated gently. After the first vigorous reaction, the mixture was boiled for 3h and then evaporated to remove the excess nitrobenzene. The solution was added a saturated aqueous solution of sodium bicarbonate until pH=7-8, then the solution was filtered and extracted with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The solid was purified by flash column chromatography to give a yellow solid, which was further washed with petroleum ether to give 7.5 g of 6-bromo-7-methyl-quinoline (31% yield): 1H NMR (CDCl3): 2.60 (s, 3H), 7.36 (m, IH), 7.96 (s, IH), 8.04 (m, 2H), 8.89 (m, IH).

Reference： [1]Patent: WO2008/51808,2008,A2 .Location in patent: Page/Page column 79-80

2
[ 122759-89-1 ]
[ 84583-52-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium hydroxide;tris-(dibenzylideneacetone)dipalladium(0); XPhos; In 1,4-dioxane; water; at 100℃; for 2.0h;	Intermediate 9: Trifluoromethanesulfonic acid 7-methyl-quinolin-6-yl ester; Step 1: 7-Methyl-quinolin-6-ol; [0315] A vial was purged with nitrogen and charged with <strong>[122759-89-1]6-bromo-7-methyl-quinoline</strong> (2.0 g, 9 mmol), grounded KOH (2.02 g, 36 mmol), tris(dibenzylideneacetone)dipalladium(0) (165 mg, 0.18 mmol), and X-Phos (Strem ligand, 343 mg, 0.72 mmol). Water (6 mL) and 1,4-dioxane (6 mL) were added, and the reaction mixture was stirred at 1000C for 2h. After cooling to room temperature, the reaction mixture was acidified to pH 5 with 1 N aqueous HCl and extracted with ethyl acetate (2x). The combined organic layers were adsorbed on silica gel. Purification by flash chromatography on silica gel using a gradient of 0-100% ethyl acetate/hexane afforded 1.37 g of 7-methyl- quinolin-6-ol as a light yellow solid (95% yield): 1H NMR (DMSO-Jd) delta 2.34 (s, 3H), 7.12 (s, IH), 7.32 (dd, IH), 7.73 (s, IH), 8.07 (dd, IH), 8.60 (dd, IH), 10.1 (broad s, IH); MS (m/z) 160 [M+H]+.

Reference： [1]Patent: WO2008/51808,2008,A2 .Location in patent: Page/Page column 84

3
[ 122759-89-1 ]
copper(l) cyanide [ No CAS ]
[ 1431869-12-3 ]

Yield	Reaction Conditions	Operation in experiment
		Step A: 7-Methyl-2-oxo-l, 2-dihydroquinoline-6-carbonitrileA mixture of 6-bromo-7-methylquinolin (10 g, 42.0 mmol, prepared following J Med. Chem. 1988, 31, 2048.), N-methyl-2-pyrrolidinone (32 mL), and CuCN (1 1 g, 0.13 mol) was stirred at 20 C overnight and then at reflux temperature (202 C) for 7 h. The mixture was poured into water (250 mL) and filtered, and the solid was washed twice with water to furnish 7-Methyl-2- oxo-1 , 2-dihydroquinoline-6-carbonitrile.

Reference： [1]Patent: WO2013/62900,2013,A1 .Location in patent: Page/Page column 19; 20

4
[ 122759-89-1 ]
[ 1431869-53-2 ]

Reference： [1]Patent: WO2013/62900,2013,A1

5
[ 122759-89-1 ]
[ 1431869-13-4 ]

Reference： [1]Patent: WO2013/62900,2013,A1

6
[ 122759-89-1 ]
[ 1431869-14-5 ]

Reference： [1]Patent: WO2013/62900,2013,A1

7
[ 122759-89-1 ]
[ 1431869-11-2 ]

Reference： [1]Patent: WO2013/62900,2013,A1

8
[ 6933-10-4 ]
[ 56-81-5 ]
[ 122759-89-1 ]
6-bromo-5-methylquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%; 20%	With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 120 - 130℃; for 1.5h;	The raw materials 3,5-difluoroaniline G-1 (5.6 g, 27 mmol) and sodium 3-nitrobenzenesulfonate (7.2 g, 32 mmol) Was added to a mixed solution of concentrated sulfuric acid (15 mL) and water (6 mL) After heating to an internal temperature of 120 C, glycerol (7.4 g, 80 mmol) After the addition was completed, the temperature was raised to 130 C and reacted for 1.5h, then cooled. The reaction was poured into crushed ice, concentrated ammonia water to adjust the pH to 5 ~ 6, the precipitated solid was filtered off, washed with water, After drying, column chromatography gave 3.82 g of white solid compound G-2 in 58% yield. A mixture of 6-bromo-7-methylquinoline (I-2) and 6-bromo-5-methylquinoline (J-1) was synthesized. Then separated by supercritical preparative chromatography (SFC), IC-H column, mobile phase: isopropanol / carbon dioxide = 18/82, detection wavelength: 254nm. The first fraction was collected as 6-bromo-7-methylquinoline (I-2) as a white solid, yield: 25%. The second fraction was collected as a 6-bromo-5-methylquinoline (J-1) white solid in a yield of 20%
	With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 110 - 140℃;	General procedure: 4-Bromo-3-fluoroaniline (D-1, 5.0 g, 26.3 mmol) and sodium 3-nitrobenzenesulfonate (7.1 g, 31.6 mmol)were added to the mixture of H2SO4 (20ml) and H2O (10ml). When the mixture was heated to 110C, Glycerin (7.27 g,78.9 mmol) was added slowly, then the reactionwas stirred at 140C overnight. After cooled to rt, the mixture was poured to alarge amount of ice water, concentrated ammonia water was added to adjust topH=8, then extracted with EtOAc, washed with brine and dried over anhydrous Na2SO4,then purified by flash column chromatography to afford6-bromo-7-fluoroquinoline as white solid (D-2,4.8 g, 81% yield). LC-MS (ESI): [M+H]+=226. 1H NMR (400MHz, CDCl3) delta 8.93 (dd, J1=4.4Hz, J2=1.6 Hz, 1H),8.12-8.02 (m, 2H), 7.81 (d, J=9.6 Hz, 1H), 7.41 (dd, J1=8.4 Hz, J2=4.4 Hz, 1H).

Reference： [1]Patent: CN105968115,2016,A .Location in patent: Paragraph 0492; 0518-0520
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

9
[ 122759-89-1 ]
6-bromo-N<SUP>2</SUP>-(1-(7-methylquinolin-6-yl)ethyl)pyrazine-2,3-diamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

10
[ 122759-89-1 ]
6-(1-(6-bromo-1H-imidazo[4,5-b]pyrazin-1-yl)ethyl)-7-methylquinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

11
[ 122759-89-1 ]
1-(7-methylquinolin-6-yl)ethan-1-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

12
[ 122759-89-1 ]
6-(1-bromoethyl)-7-methylquinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

13
[ 122759-89-1 ]
2-(1-(7-methylquinolin-6-yl)ethyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

14
[ 122759-89-1 ]
7-methyl-6-(1-(6-(1-methyl-1H-pyrazol-4-yl)-1H-imidazo[4,5-b]pyrazin-1-yl)ethyl)quinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

15
[ 122759-89-1 ]
7-methyl-6-(1-(6-(pyridin-4-yl)-1H-imidazo[4,5-b]pyrazin-1-yl)ethyl)quinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

16
[ 122759-89-1 ]
2-fluoro-4-(1-(1-(7-methylquinolin-6-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-6-yl)benzoic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

17
[ 122759-89-1 ]
2-fluoro-N-methyl-4-(1-(1-(7-methylquinolin-6-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-6-yl)benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

18
[ 122759-89-1 ]
2-fluoro-4-(1-(1-(7-methylquinolin-6-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-6-yl)benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

19
[ 122759-89-1 ]
7-methyl-6-(1-(6-(quinolin-3-yl)-1H-imidazo[4,5-b]pyrazin-1-yl)ethyl)quinoline [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

20
[ 122759-89-1 ]
1-(7-methylquinolin-6-yl)ethan-1-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4281 - 4290

21
[ 122759-89-1 ]
[ 97674-02-7 ]
1-(7-methylquinolin-6-yl)ethan-1-one [ No CAS ]