[ CAS No. 41037-28-9 ]

Name: 41037-28-9|6-Bromo-4-methylquinoline|97%
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Product Details of [ 41037-28-9 ]

CAS No. :	41037-28-9	MDL No. :	MFCD09258893
Formula :	C₁₀H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XBZQSJLYRMZRSZ-UHFFFAOYSA-N
M.W :	222.08	Pubchem ID :	12475362
Synonyms :

Calculated chemistry of [ 41037-28-9 ]

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) :	-5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.33
Log Po/w (XLOGP3) :	3.3
Log Po/w (WLOGP) :	3.31
Log Po/w (MLOGP) :	2.85
Log Po/w (SILICOS-IT) :	3.6
Consensus Log Po/w :	3.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.91
Solubility :	0.0272 mg/ml ; 0.000122 mol/l
Class :	Soluble
Log S (Ali) :	-3.25
Solubility :	0.126 mg/ml ; 0.000567 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 :	1.18

Safety of [ 41037-28-9 ]

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

Application In Synthesis of [ 41037-28-9 ]

* 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 [ 41037-28-9 ]
Downstream synthetic route of [ 41037-28-9 ]

[ 41037-28-9 ] Synthesis Path-Upstream 1~1

1
[ 78-94-4 ]
[ 106-40-1 ]
[ 41037-28-9 ]

Reference： [1] Tetrahedron Letters, 2000, vol. 41, # 4, p. 531 - 533
[2] Tetrahedron, 2003, vol. 59, # 6, p. 813 - 819
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 7, p. 2302 - 2306
[4] Patent: WO2004/48382, 2004, A1, . Location in patent: Page 7

[ 41037-28-9 ] Synthesis Path-Downstream 1~40

1
[ 41037-28-9 ]
[ 100-10-7 ]
[ 109555-19-3 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 682

2
[ 41037-28-9 ]
[ 762-04-9 ]
(4-Methyl-quinolin-6-yl)-phosphonic acid diethyl ester [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1986,vol. 56,p. 2214 - 2216
Zhurnal Obshchei Khimii,1986,vol. 56,p. 2503 - 2507

3
[ 78-94-4 ]
[ 106-40-1 ]
[ 41037-28-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In 1,4-dioxane; for 1h;Heating / reflux;	Stir a solution OF 4-BROMO-PHENYLAMINE (1 EQ), in 1,4-dioxane and cool to approximately 12 C. Slowly add sulfuric acid (2 eq) and heat at reflux. Add methylvinyl ketone (1.5 eq) dropwise into the refluxing solution. Heat the solution for 1 hour after addition is complete. Evaporate the reaction solution to dryness and dissolve in methylene chloride. Adjust the solution to pH 8 with 1 M sodium carbonate and extract three times with water. Chromatograph the residue on SI02 (70/30 hexane/ethyl acetate) to obtain the desired subtitled INTERMEDIATE. MS ES+ M/E = 158. 2 (M+1).

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 531 - 533
[2]Tetrahedron,2003,vol. 59,p. 813 - 819
[3]Journal of Medicinal Chemistry,2008,vol. 51,p. 2302 - 2306
[4]Patent: WO2004/48382,2004,A1 .Location in patent: Page 7
[5]Bioorganic and Medicinal Chemistry Letters,2020,vol. 30

5
[ 13602-11-4 ]
[ 41037-28-9 ]
2-(6-bromoquinolin-4-yl)-1-(6-methylpyridin-2-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.8%		Dissolve 6-bromo-4-methyl-quinoline (38.5 g, 153 mmol) in 600 mL dry THF. Cool to-70 C and treat with the dropwise addition of 0.5 M potassium hexamethyldisilazane (KN (SiMe3) 2 (400 mL, 200 mmol) over 2 hours while keeping the temperature BELOW-65 C. Stir the resultant solution at-70C for 1 hour and add a solution of 6-methylpyridine-2-carboxylic acid methyl ester (27.2, 180 mmol) in 100 mL dry THF dropwise over 15 minutes. During the addition, the mixture will turn from dark red to pea-green and form a precipitate. Stir the mixture at-70C over 2 hours then allow it to warm to ambient temperature with stirring for 5 hours. Cool the mixture then quench with 12 N HC1 to PH=L. Raise the pH to 9 with solid potassium carbonate. Decant the solution from the solids and extract twice with 200 mL ethyl acetate. Combine the organic extracts, wash with water and dry over potassium carbonate. Stir the solids in 200 mL water and 200 mL ethyl acetate and treat with additional potassium carbonate. Separate the organic portion and dry with the previous ethyl acetate extracts. Concentrate the solution in vacuo to a dark oil. Pass the oil through a 300 mL silica plug with methylene chloride then ethyl acetate. Combine the appropriate fractions and concentrate in vacuo to yield an amber oil. Rinse the oil down the sides of the flask with methylene chloride then dilute with hexane while swirling the flask to yield 38.5 g (73.8 %) of the desired subtitled intermediate as a yellow solid. MS ES+ = 341 (M+1).

Reference： [1]Patent: WO2004/48382,2004,A1 .Location in patent: Page 8
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 2302 - 2306

6
[ 41037-28-9 ]
C₁₁H₈BrNOS [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 8871 - 8874

7
[ 41037-28-9 ]
[ 1619994-39-6 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 8871 - 8874

8
[ 41037-28-9 ]
[ 463-71-8 ]
(Z)-3-(5-bromo-2-isothiocyanatophenyl)but-2-enal [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 8871 - 8874

9
[ 41037-28-9 ]
[ 542-91-6 ]
6-bromo-3-(diethylsilyl)-4-methyl-1,2,3,4-tetrahydroquinoline [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 16780 - 16783

10
[ 41037-28-9 ]
6-bromo-4-(difluoromethyl)quinoline [ No CAS ]

Reference： [1]Chemical Science,2018,vol. 9,p. 5608 - 5613
[2]Patent: EP3569596,2019,A1

11
[ 41037-28-9 ]
[ 73183-34-3 ]
(4-methylquinolin-6-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 20h;Inert atmosphere;	General procedure: In a pressure tube, 5-bromo-1 H-indazole (400 mg, 2 mmol), bis(pinacolato)diboron (773 mg, 3 mmol) and KOAc (598 mg, 6 mmol) were dissolved in 40 mL of dry DMF and sparged with argon for 10 mi Pd(dppf)012 (149 mg, 0.2 mmol) was added in one portion, and the reactionmixture was sparged with argon for additional 3 mm. The pressure tube was capped and the reaction mixture was heated at 10000 overnight. After full conversion (monitored by LOMS), the reaction mixture was filtered throught Celite and the filtrate was concentrated under reduced pressure. The residue was dissolved in EtOAc and co-evaporated with silica. Product was purified by column chromatography, eluting with hexane:EtOAc (0-50%) to afford the title product asa white solid (0.5 g, 2 mmol, quant.). ESI-MS: 245.1 [M+H]+. 1 H NMR (300 MHz, DMSO-d6) 613.15 (s, 1H), 8.16 (s, 1H), 8.12 (s, 1H), 7.61 (dd, J = 8.4, 1.1 Hz, 1H), 7.52 (dt, J = 8.4, 1.0 Hz,1H), 1.31 (s, 12H).

Reference： [1]Patent: WO2019/2606,2019,A1 .Location in patent: Page/Page column 78; 145

12
[ 41037-28-9 ]
8-amino-6-(3-fluorophenyl)-5-(4-methylquinolin-6-yl)imidazo[1,2-a]pyrazine-2-carboxamide [ No CAS ]

Reference： [1]Patent: WO2019/2606,2019,A1

13
[ 41037-28-9 ]
6-bromoquinoline-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With selenium(IV) oxide; In 1,4-dioxane; water; at 80℃; for 16h;	Compound 14a (1.0 g, 4.50 mmol) was dissolved in 20 mL of 1,4-dioxane. The reaction solution was added with 2 mL of water, followed by addition of selenium dioxide (1.5 g, 13.51 mmol). The reaction solution was stirred at 80C for 16 hours, and then cooled to room temperature, added with saturated sodium bicarbonate solution, and extracted with ethyl acetate (30 mL×3). The organic phases were combined, washed with saturated sodium chloride solution, dried over sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with elution system B to obtain the title compound 51a (670 mg), yield: 63.0%.

Reference： [1]Patent: EP3569596,2019,A1 .Location in patent: Paragraph 0280; 0281
[2]Journal of Organic Chemistry,2019,vol. 84,p. 4040 - 4049

14
[ 41037-28-9 ]
[ 420-37-1 ]
6-bromo-1-methoxy-4-methylquinolin-1-ium tetrafluoroborate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 4040 - 4049

15
[ 41037-28-9 ]
[ 25015-63-8 ]
6-bromo-4-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydroquinoline [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 6320 - 6325

16
[ 109-99-9 ]
[ 41037-28-9 ]
4-(6-bromo-4-methylquinolin-2-yl)butan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid; lithium bromide; In water; chlorobenzene; for 60h;Irradiation; Inert atmosphere;	General procedure: Step 1: Put quinoline compounds (see Table 1 for specific substances), lithium bromide, water, acid (see Table 1 for specific substances) and add to the reaction vessel. The catalysts (see Table 1 for specific substances) and organic solvents (specific materials) See Table 1) Add to the reaction vessel and mix well;Step 2: The reaction vessel is subjected to inert gas extraction three times, an ether compound is added, and the reactor is uniformly irradiated with blue light (such as a blue LED lamp), and the quinoline compound and the ether compound are reacted in a solvent, and the reaction is continued. The time stated in 1;Step 3: Purification is carried out after completion of the reaction.

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5643 - 5647
[2]Patent: CN109776406,2019,A .Location in patent: Paragraph 0056-0062; 0164

17
[ 542-69-8 ]
[ 41037-28-9 ]
C₁₄H₁₇BrN⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetonitrile; at 70℃; for 6h;	(1) 0.5 g of <strong>[41037-28-9]6-bromo-4-methylquinoline</strong> was weighed into a 50 ml flask, and 20 ml of dry acetonitrile was added.After being dissolved, 0.414 g of iodine is added.The mixture was reacted under reflux of 70 C for 6 hours.After the reaction was completed, most of the acetonitrile was removed under reduced pressure distillation, and the product was dropped into anhydrous diethyl ether.A yellow solid precipitated. After suction filtration, the filter cake was washed 3 times with anhydrous diethyl ether to obtain a pure product quinoline compound in a yield of 90%.

Reference： [1]Patent: CN110003103,2019,A .Location in patent: Paragraph 0037-0038

18
[ 41037-28-9 ]
[ 111-83-1 ]
C₁₈H₂₅BrN⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In acetonitrile; at 70℃; for 6h;	(1) 0.5 g of <strong>[41037-28-9]6-bromo-4-methylquinoline</strong> was weighed into a 50 ml flask, and 20 ml of dry acetonitrile was added. After the dissolution, 0.5 g of bromooctane was added, and the mixture was reacted under reflux at 70 C for 6 hours. After completion of the reaction, most of the acetonitrile was removed under reduced pressure and the product was poured into anhydrous diethyl ether. After suction filtration, the filter cake was washed three times with anhydrous diethyl ether to give a pure product quinoline compound with a yield of 92%.

Reference： [1]Patent: CN110003103,2019,A .Location in patent: Paragraph 0041-0042

19
[ 41037-28-9 ]
[ 111-83-1 ]
C₄₃H₄₆Br₂N₄O [ No CAS ]

Reference： [1]Patent: CN110003103,2019,A

20
[ 74-96-4 ]
[ 41037-28-9 ]
C₁₂H₁₃BrN⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In acetonitrile; at 60℃; for 6h;	(1) 0.5 g of <strong>[41037-28-9]6-bromo-4-methylquinoline</strong> was weighed into a 50 ml flask, and 20 ml of dry acetonitrile was added. After the solution was dissolved, 0.24 g of ethyl bromide was added, and the mixture was reacted under heating at 60 C for 6 hours under reflux. After completion of the reaction, most of the acetonitrile was removed under reduced pressure and the product was poured into anhydrous diethyl ether. After suction filtration, the filter cake was washed 3 times with anhydrous diethyl ether to obtain a pure product quinoline compound in a yield of 90%.

Reference： [1]Patent: CN110003103,2019,A .Location in patent: Paragraph 0045-0046; 0049-0050; 0053-0054; 0057-0058; 0061

21
[ 41037-28-9 ]
C₃₅H₃₀Br₂N₄O [ No CAS ]

Reference： [1]Patent: CN110003103,2019,A
[2]Patent: CN110003103,2019,A

22
[ 109-65-9 ]
[ 41037-28-9 ]
C₁₄H₁₇BrN⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In acetonitrile; at 70℃; for 6h;	(1) 0.5 g of <strong>[41037-28-9]6-bromo-4-methylquinoline</strong> was weighed into a 50 ml flask, and 20 ml of dry acetonitrile was added.After dissolution, 0.308 g of bromobutane was added.The mixture was reacted under reflux of 70 C for 6 hours.After the reaction was completed, most of the acetonitrile was removed under reduced pressure distillation, and the product was dropped into anhydrous diethyl ether.A yellow solid precipitated. After suction filtration, the filter cake was washed 3 times with anhydrous diethyl ether to obtain a pure product quinoline compound.The yield was 95%.

Reference： [1]Patent: CN110003103,2019,A .Location in patent: Paragraph 0029-0031

23
[ 41037-28-9 ]
[ 590-86-3 ]
C₁₅H₁₈BrN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With methanesulfonic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; lithium bromide; In dimethyl sulfoxide; at 20℃; for 60h;	General procedure: Step 1: Mix 4-methylquinoline compounds (see Table 1 for specific substances) andAdd fatty aldehyde compounds (see Table 1 for specific substances) to the reaction vessel.Iridium-containing catalysts (see Table 1 for specific substances),Additives (see Table 1 for specific substances),Organic acids (see Table 1 for specific substances) and organic solvents (see Table 1 for specific substances) are added to the reaction vessel.Step 2: The reaction vessel is heated uniformly (such as in a water bath) to the temperature described in Table 1 and irradiated under blue light. The 4-methylquinoline compound and the fatty aldehyde compound are reacted in a solvent, and the reaction is continued in Table 1. The time described in the description; the reaction atmosphere to be explained is selected to be nitrogen protection.Step 3: Purification step.

Reference： [1]ACS Catalysis,2020,vol. 10,p. 154 - 159
[2]Patent: CN110272383,2019,A .Location in patent: Paragraph 0046-0051; 0052; 0076

24
[ 41037-28-9 ]
[ 73183-34-3 ]
4-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.5%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,2-dimethoxyethane; at 80℃; for 12h;Inert atmosphere;	6-Bromo-4-methylquinoline 14a (444 mg, 2 mmol, prepared according to the known method disclosed in "Tetrahedron, 2003, 59(6), 813-819"), bis(pinacolato)diboron (762 mg, 3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (292 mg, 0.40 mmol) and potassium acetate (588 mg, 6.00 mmol) were dissolved successively in 20 mL of dimethyl ether under an argon atmosphere. The reaction solution was heated to 80C, and stirred for 12 hours. The reaction was stopped, and the reaction solution was cooled to room temperature and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 14b (460 mg), yield: 85.5%. MS m/z (ESI): 270.4 [M+1].

Reference： [1]Patent: EP3569596,2019,A1 .Location in patent: Paragraph 0176; 0177

25
[ 41037-28-9 ]
6-(4-methylquinolin-6-yl)-5-phenyl-1,2,4-triazin-3-amine [ No CAS ]