53967-21-8|6-(Bromomethyl)quinoxaline| Ambeed

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Quality Control of [ 53967-21-8 ] Purity: 97% SDS Specification

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Product Details of [ 53967-21-8 ]

CAS No. :	53967-21-8
Formula :	C₉H₇BrN₂
M.W :	223.07
SMILES Code :	BrCC1=CC=C2N=CC=NC2=C1
MDL No. :	MFCD11559042
InChI Key :	DMLZDWGHHYSKGY-UHFFFAOYSA-N
Pubchem ID :	10214510

Safety of [ 53967-21-8 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P261-P280-P305+P351+P338-P310
Class:	8
UN#:	1759
Packing Group:	Ⅲ

Application In Synthesis of [ 53967-21-8 ]

* 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 [ 53967-21-8 ]

[ 53967-21-8 ] Synthesis Path-Downstream 1~23

1
[ 110-91-8 ]
[ 53967-21-8 ]
[ 53967-22-9 ]

References: [1]Journal of Heterocyclic Chemistry,1974,vol. 11,p. 595 - 597.

2
[ 130723-09-0 ]
[ 53967-21-8 ]
[ 133739-03-4 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2600 - 2609.

3
[ 6344-72-5 ]
[ 53967-21-8 ]

Yield	Reaction Conditions	Operation in experiment
35%	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane; for 48h;Reflux;	A mixture of 6-methylquinoxaline (2.0 g, 13.9 mmol), N-bromosuccinimide (3.0 g, 16.9 mmol), and benzoyl peroxide (411 mg, 1.7 mmol) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux for 2 days. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (1 x 100 mL) and brine (1 x 100 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-30% EtOAc/hexanes), affording 6- (bromomethyl)quinoxaline (1.10 g, 35% yield).
	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 18h;Inert atmosphere; Reflux;	Intermediate 17: 6-(bromomethyl)quinoxaline A mixture of 6-methylquinoxaline (300 mg), NBS (370 mg) and benzoyl peroxide (5.04 mg) in carbon tetrachloride (8 ml.) was heated at reflux under an atmosphere of argon for 18 hr. The reaction mixture was cooled to RT, filtered and concentrated under reduced pressure to give a brown oil. The crude product was purified by column chromatography (Biotage SP4, 40+M column, 20-100% EtOAc / isohexane. The fractions containing product were combined and concentrated under reduced pressure to give the title compound (243 mg) as a white solid, m/z [M+H]+: 223.1 / 225.0. Retention time 0.80 min (LC/MS method 3).
	With N-Bromosuccinimide; dibenzoyl peroxide;	Example 292 Synthesis of 6-(bromomethyl)quinoxaline. To a solution of 6-methylquinoxaline (5 g, 34.7 mmol) in DCE (100 mL) was added NBS (7.12 g, 40 mmol) and benzoyl peroxide (840 mg, 3.47 mmol). The reaction mixture was stirred at 85 C. for 16 h under nitrogen. H2O (100 mL) was added, and the mixture was extracted with DCM (150 mL*3). The combine organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give the crude product which was purified by silica gel chromatography (PE/EtOAc=1/1) to give 6-(bromomethyl)quinoxaline as a yellow solid. (5.5 g, 71%). ESI-MS [M+H]+: 224.1.

References: [1]ChemMedChem,2017,vol. 12,p. 257 - 270.
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 617 - 628.
[3]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 111.
[4]Patent: WO2011/23753,2011,A1 .Location in patent: Page/Page column 74-75.
[5]Patent: US2019/284182,2019,A1 .

4
[ 372-31-6 ]
[ 53967-21-8 ]
ethyl 6-quinoxolinyl-α-(trifluoroacetyl)propanoate [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 617 - 628.

Yield	Reaction Conditions	Operation in experiment
		g. 6-Bromomethylquinazoline, used as a starting material, was prepared from 6-methylquinazoline (J. Chem. Soc., 1962, 561) using the procedure described in J. Het Chem., 1974, 11, 595 for the preparation of 6-bromomethylquinoxaline from 6-methylquinoxaline.
		i. 6-Bromomethylquinazoline, used as the alkylating agent, was prepared from 6-methylquinazoline (J. Chem. Soc., 1962, 561) using the procedure described in J. Het. Chem., 1974, 11, 595 for the preparation of 6-bromomethylquinoxaline from 6-methylquinoxaline.
		g. 6-Bromomethylquinazoline, used as a starting material, was prepared from 6-methylquinazoline (J. Chem. Soc ., 1962, 561) using the procedure described in J. Het. Chem. , 1974, 11 , 595 for the preparation of 6-bromomethylquinoxaline from 6-methylquinoxaline.

6
2‐(4‐tert‐butylphenyl)‐4‐(piperazin‐1‐yl)‐1H‐benzo[d]imidazole [ No CAS ]
[ 53967-21-8 ]
[ 872002-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 20℃; for 22h;	2-(4-tert-butylphenyl)-4-[4-(6-quinoxalyl)methyl]piperazin-1-yl}benzimidazole; To a suspension of 2-(4-t-butylphenyl)-4-piperazin-1-yl-1H-benzimidazole (49.5 g, 0.148 mol) and potassium carbonate (40.0 g, 0.29 mol) in acetone (0.800 L, EM) was added <strong>[53967-21-8]6-bromomethylquinoxaline</strong> (33.0 g, 0.148 mol) as a solid in one portion at room temperature. The reaction mixture was stirred for 22 h at ambient temperature. The product precipitated out of solution was separated by filtration; the cake was washed with 30 mL of acetone, then triturated with 0.8 L of water and filtered again. The trituration procedure was repeated two more times. The resulting solid was dried in a stream of air first, then in a vacuum desiccator over CaSO4 to give 70 g (0.147 mol) of the desired product as a white amorphous solid. Purity 98% (HPLC at 254 nm).

References: [1]Patent: US2005/282820,2005,A1 .Location in patent: Page/Page column 18.

7
[ 6344-72-5 ]
C₉H₆Br₂N₂ [ No CAS ]
[ 53967-21-8 ]

Yield	Reaction Conditions	Operation in experiment
23%; 77%	With N-Bromosuccinimide; dibenzoyl peroxide; In benzene; for 5h;Heating / reflux;	Example 9 6-Bromomethylquinoxaline: A mixture of 6-methylquinoxaline (1.5 g, 10.4 mmol), N-bromosuccinimide (2.2 g, 12.5 mmol) and benzoylperoxide (0.30 g, 1.25 mmol) in benzene (35 mL) was stirred rapidly and heated to reflux for 5 h. Upon cooling the mixture was diluted with ethyl acetate (25 mL), washed with 1N sodium hydroxide solution (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was dried (MgSO4) and evaporated to a crystalline solid (2.5 g, 77% desired product, 23% alpha,alpha-dibrominated product as determined by 1H NMR). The mixture was used in subsequent reactions.
23%; 77%	With N-Bromosuccinimide; dibenzoyl peroxide; In benzene; for 5h;Heating / reflux;	6-Bromomethyl-quinoxaline: A mixture of 6-methylquinoxaline (1.5 g, 10.4 mmol), N-bromosuccinimide (2.2 g, 12.5 mmol) and benzoylperoxide (0.30 g, 1.25 mmol) in benzene (35 mL) was stirred rapidly and heated to reflux for 5 h. Upon cooling, the mixture was diluted with ethyl acetate (25 mL), washed with IN sodium hydroxide solution (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was dried (MgSO4) and evaporated to a crystalline solid (2.5 g, 77% desired product, 23% alpha,alpha-dibrominated product as determined by 1H NMR). The mixture was used in subsequent reactions.
36%	With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2h;Heating / reflux;	6-Bromomethylquinoxaline (1) (De Selms, R. C.; Greaves, R. J., Scheigh, W. R. J. Het. Chem. 1974, 11, 595); Bromomethylquinoxaline is unstable and decomposes when stored for long time. It should be used up within a day or two of its preparation. To a clear solution of 6-methylquinoxaline (60 g, 0.416 mol) in 550 mL of CCl4 was added in one portion solid NBS (Aldrich, 81.5 g, 0.458 mol, 1.1 eq) and AlBN (Aldrich, 1.6 g, 9.7 mmol, 2.3 mol %). The resulting mixture was heated at reflux for 2 hr and cooled to rt. The precipitate of succinimide was removed by filtration. The filtrate was evaporated on rotary evaporator until solid begins to crystallize out of the solution. Remaining mixture was left at rt for 2 hr, then the crystallized product was filtered off, washed with small amount of hexanes-CCl4 mixture (ca. 20:1) and dried in vacuum. The isolated solid contained just traces of the di-bromo side-product and was used in the following step without further purification. Yield 33.3 g (36%) as colorless crystals.

References: [1]Patent: US2006/264631,2006,A1 .Location in patent: Page/Page column 37.
[2]Patent: US2006/270848,2006,A1 .Location in patent: Page/Page column 39.
[3]Patent: US2005/282820,2005,A1 .Location in patent: Page/Page column 18.

8
[ 53967-21-8 ]
[ 488834-75-9 ]

Yield	Reaction Conditions	Operation in experiment
		The light reddish solution of <strong>[53967-21-8]6-bromomethyl-quinoxaline</strong> was used to prepare 6-hydroxymethyl-quinoxaline as shown in the examples below.

References: [1]Patent: US6548670,2003,B1 .

9
[ 6344-72-5 ]
[ 53967-21-8 ]
[ 488834-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; dibenzoyl peroxide; In 1,2-dichloro-ethane;	Example 3 Preparation of a Solid Sample of 6-bromomethyl-quinoxaline In a 100 ml flask, 6-methyl-quinoxaline (2.5 g, 17.4 mmol) was dissolved together with N-bromosuccinimide (4.63 g, 19 mmol) and benzoyl peroxide (0.3 g, 1.24 mmol) in 70 g of 1,2-dichloroethane. The solution was refluxed for 150 minutes and analyzed. The concentrations of the reactants and some of their molar ratios are shown below: The solution was cooled in the freezer overnight and the solid residue was separated by filtration. The solid was washed with pentane and the washings were combined with the liquid fraction. The clear reddish solution was then vacuum dried to give an orange solid that was used in the preparation of 6-hydroxymethyl-quinoxaline.

References: [1]Patent: US6548670,2003,B1 .

10
[ 915135-27-2 ]
[ 53967-21-8 ]
6-({4-[2-(4-tert-butylphenyl)-1,3-benzoxazol-7-yl]piperazin-1-yl}methyl)quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 95℃;	Example 25 6-({4-[2-(4-tert-butylphenyl)-1,3-benzoxazol-7-yl]piperazin-1-yl}methyl)quinoxaline: To a suspension of 2-(4-tert-butylphenyl)-7-piperazin-1-yl-1,3-benzooxazole 23.5 mg, 0.070 mmol) and <strong>[53967-21-8]6-bromomethylquinoxaline</strong> (17.2 mg, 0.077 mmol) in CH3CN (anh., 10 mL) was added ethyldiisopropylamine (0.015 mL, 0.084 mmol). The mixture was heated in a 95 C. bath overnight. The reaction was cooled to room temperature and concentrated in vacuo. The residue was adsorbed onto silica gel. Silica gel chromatography using a gradient of 25% EtOAc/hexane to 50% EtOAc/hexane then 100% EtOAc afforded the title compound (23.2 mg) as an ivory powder. MS (ESI) m/z 478 [M+H]+; HPLC Method C, r.t.=10.9 min (98.9% a210-370 nm; 97.4% a 236 nm).

References: [1]Patent: US2006/264631,2006,A1 .Location in patent: Page/Page column 41-42.

11
[ 915306-85-3 ]
[ 53967-21-8 ]
6-{4-[2-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyridin-5-yl]-piperazin-1-ylmethyl}-quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; at 20℃;	6-{4-[2-(4-tert-Butyl-phenyl)-imidazo[1,2-a]pyridin-5-yl]-piperazin-1-ylmethyl}-quinoxaline: 2-(4-tert-Butyl-phenyl)-5-piperazin-1-yl-imidazo[1,2-a]pyridine (0.086 g, 0.258 mmol) was dissolved in DMSO (1 mL) and treated with <strong>[53967-21-8]6-bromomethyl-quinoxaline</strong> (0.072 g, 0.323 mmol) followed by diisopropylethylamine (0.046 mL, 0.258 mmol). The mixture was stirred at room temperature overnight and diluted with ethyl acetate (10 mL). The solution was washed with water and saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the crude product. Purification by flash silica gel chromatography (40-50% acetone/hexanes) gave 0.0362 g (29%) of the title compound. HPLC (Method B): r.t.=9.6 min., purity 100% at 210-370 nm, 96.0% at 238 nm. HRMS: calcd for C30H32N6+H+, 477.27612; found (ESI, [M+H]+), 477.2786.

References: [1]Patent: US2006/270848,2006,A1 .Location in patent: Page/Page column 42.

12
[ 56-04-2 ]
[ 53967-21-8 ]
[ 1256559-19-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In ethanol; at 20℃;	A mixture of <strong>[53967-21-8]6-(bromomethyl)quinoxaline</strong> (900 mg, 4.0 mmol), 6-methyl-2- sulfanylpyrimidin-4-ol (440 mg, 3.1 mmol), and triethylamine (1.1 mL, 7.8 mmol) in absolute ethanol (20 mL) was stirred at room temperature overnight. The reaction mixture was evaporated and then co-evaporated with EtOAc. The solid residue was treated with water (100 mL). The solid product was recovered by filtration, washed with water (2 x 20 mL), diethyl ether (3 x 20 mL), and hexanes (3 x 20 mL), and then dried in vacuo, affording 6-methyl-2-[(quinoxalin-6-ylmethyl)sulfanyl]pyrimidin-4-ol (658 mg, 75% yield). The product was used without further purification.

References: [1]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 111.

13
[ 1268628-82-5 ]
[ 53967-21-8 ]
2,2-difluoro-4-(6-quinoxalinylmethyl)-8-[2,2,2-trifluoro-1-hydroxyethyl]-2H-1,4-benzoxazin-3(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Compound 26: 2,2-difluoro-4-(6-quinoxalinylmethyl)-8-[(1 /?)-2,2,2-trifluoro-1 - hydroxyethyl]-2H-1,4-benzoxazin-3(4H)-one and compound 27: 2,2-difluoro-4-(6- quinoxalinylmethyl)-8-[(1 S)-2,2,2-trifluoro-1 -hydroxyethyl]-2H-1 ,4-benzoxazin- 3(4H)-one R-stereoisomer S-stereoisomer6-(Bromomethyl)quinoxaline (50 mg; may be prepared as described in intermediate 17) was added to a solution of 2,2-difluoro-8-(2,2,2-trifluoro-1-hydroxyethyl)-2H-1 ,4- benzoxazin-3(4H)-one (63.5 mg; may be prepared as described in intermediate 5) in DMF (3 ml_). Potassium carbonate (75 mg) and potassium iodide (1.860 mg) were added. The reaction was stirred overnight at RT, under argon. Then water (20 ml.) was added to the reaction mixture, and the new mixture was extracted 3 times with 20 ml. of EtOAc. The combined organic phases were washed 3 times with 20 ml. of water, and finally with 25 ml. of brine. Then this phase was dried over anhydrous magnesium sulfate, and the solvent was evaporated to give a colorless oil and crystals. The crude product was purified by MDAP to give 26.2 mg of white crystals. The enantiomers were resolved using a Chiracel OJ column eluting with heptane / ethanol 50:50 (v/v) pump mixed. Under these conditions the faster-running enantiomer (1 1.6 mg; compound 26 or 27) and the faster-running enantiomer (12.4 mg; compound 26 or 27) were obtained in > 99.8% enantiomeric excess, m/z [M+H]+: 426.1. Retention time 1.00 min (LC/MS method 3).

References: [1]Patent: WO2011/23753,2011,A1 .Location in patent: Page/Page column 94-95.

14
[ 123629-42-5 ]
[ 53967-21-8 ]
C₂₄H₂₄N₄O₅ [ No CAS ]

References: [1]Acta Pharmacologica Sinica,2016,vol. 37,p. 1516 - 1524.

15
[ 130345-50-5 ]
[ 53967-21-8 ]

References: [1]Acta Pharmacologica Sinica,2016,vol. 37,p. 1516 - 1524.

16
4-(cyclopentylamino)-6-(morpholin-4-yl)-1,3,5-triazine-2-carbonitrile [ No CAS ]
[ 53967-21-8 ]
4-[cyclopentyl(quinoxalin-6-ylmethyl)amino]-6-(morpholin-4-yl)-1,3,5-triazine-2-carbonitrile [ No CAS ]

References: [1]ChemMedChem,2017,vol. 12,p. 257 - 270.

17
[ 37622-90-5 ]
[ 53967-21-8 ]
ethyl 1-(quinoxalin-6-ylmethyl)-1H-pyrazole-4-carboxylate [ No CAS ]