959121-99-4|3-Bromo-7-methoxyquinoline| Ambeed

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Quality Control of [ 959121-99-4 ] Purity: 98% SDS Specification

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Product Details of [ 959121-99-4 ]

CAS No. :	959121-99-4
Formula :	C₁₀H₈BrNO
M.W :	238.08
SMILES Code :	COC1=CC2=C(C=C1)C=C(Br)C=N2
MDL No. :	MFCD11877932
InChI Key :	BOTSUSKVHVRQAY-UHFFFAOYSA-N
Pubchem ID :	18788548

Safety of [ 959121-99-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 959121-99-4 ]

* 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 [ 959121-99-4 ]
Downstream synthetic route of [ 959121-99-4 ]

[ 959121-99-4 ] Synthesis Path-Upstream 1~4

1
[ 2065-75-0 ]
[ 536-90-3 ]
[ 959121-99-4 ]

Yield	Reaction Conditions	Operation in experiment
20%	Stage #1: at 20℃; Stage #2: With acetic acid In ethanol at 100℃; for 240 h; Stage #3: With ammonia In water	For the synthesis of this starting compound, 1.80 g (12.3 mmol, 1.1 eq) of bromomalondialdehyde was first dissolved in 30 ml of ethanol, and 1.25 ml of m-anisidine was added. This reaction mixture is stirred over night at RT and, after the addition of acetic acid (20 ml), at 100° C. for 10 days. The solvent is subsequently removed in vacuum on a rotary evaporator, and the residual solid is partitioned between a water and an ethyl acetate phase. The aqueous phase is made alkaline with an ammonia solution, and insoluble particles were filtered off. The filtrate is extracted with ethyl acetate, and the organic phase is dried over MgSO₄, filtered, and the solvent is removed in vacuum on a rotary evaporator. The product was purified by column chromatography with a mixture of hexane/ethyl acetate 8/2 as the eluent in a yield of 20percent (700 mg). C₁₀H₈BrNO; MW 237/239; ¹H-NMR (CDCl₃): δ 8.76 (d, J=2.2 Hz, 1H), 8.15 (d, J=2.2 Hz, 1H), 7.55 (d, J=9.1 Hz, 1H), 7.32 (d, J=2.5 Hz, 1H), 7.15 (dd, J=2.5 Hz, J=8.8 Hz, 1H), 3.88 (s, 3H, OMe); ¹³C-NMR (CDCl₃): δ 159.9, 150.4, 147.1, 135.9, 126.9, 123.4, 119.9, 113.6, 106.3, 54.6; IR: 2961, 1620, 1581, 1491, 1462, 1417, 1261, 1027, 796 1/cm; MS (ESI): 238-240 (M+H)⁺
3.8%	Stage #1: at 30℃; for 24 h; Stage #2: With hydrogenchloride In ethanol; water at 100℃; for 48 h;	To a solution of bromo-malonaldehyde (10 g, 66.2 mmol) in absolute ethanol (100 mL) was added 3-methoxyaniline (7.3 g, 59.6 mmol). The mixture was heated to 30 °C and stirred at that temperature for 24 h. Cone. HCl (100 mL) was added, and the reaction mixture was heated at 100°C for two days. After the mixture was concentrated and the residue was partitioned between ethyl acetate (150 mL) and saturated sodium carbonate (50 mL). The organic phase was washed with brine, dried with anhydrous Na₂S0₄ and concentrated to give a black oil, which was purified by column chromatography (PE/EA = 3/1) to give Intermediate 13 as a brown oil (500 mg, 3.8percent). MS (ESI): m/z 237.9 [M+l]⁺.

References: [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 7, p. 2158 - 2169.
[2] Patent: US2010/204234, 2010, A1, . Location in patent: Page/Page column 12.
[3] Patent: WO2012/83165, 2012, A1, . Location in patent: Page/Page column 98.

2
[ 124-41-4 ]
[ 959121-99-4 ]

Yield	Reaction Conditions	Operation in experiment
80.3%	at 80℃; for 4 h;	3-bromo-7-nitroquinoline (60.0 g, 0.24 mol) was dissolved in DMF at 80 ° C, and sodium methoxide (63.8 g, 1.18 mol) was added to the reaction mixture.After reacting for 4 h, the reaction was completed by TLC, and the methanol was spun off.The residual liquid was added to 4 times water filtration.The filter cake was dried to give 3-bromo-7-methoxyquinoline (45 g, 80.3percent).

References: [1] Patent: CN108727262, 2018, A, . Location in patent: Paragraph 0037; 0038; 0053; 0055.

3
[ 4964-76-5 ]
[ 959121-99-4 ]

References: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2358 - 2363.

4
[ 30450-62-5 ]
[ 959121-99-4 ]

References: [1] Patent: CN108727262, 2018, A, .

[ 959121-99-4 ] Synthesis Path-Downstream 1~35

1
[ 959121-99-4 ]
[ 1025369-72-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;Inert atmosphere;	To a solution of <strong>[959121-99-4]3-bromo-7-methoxyquinoline</strong> (2 g, 8.40 mmol) in DCM (42.0 mL) was added mCPBA (2.90 g, 16.8 mmol). After 1h, additional mCPBA (2.90 g, 16.8 mmol) was added and the reaction was stirred overnight. The mixture was then extracted with 10% sodium sulfite, saturated NaHCO3, and brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title product (2.04 g, 96%).
87%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃;	3- bromo 7- inethoxyquinoline ( 5 g, 2 1 mmol) was dissolv ed in dichloromethane ( 50 mL). Then 3-chloroperoxybenzoic acid (5. 1 16 g, 25.2 mmol ) was added into the mixture in fractions at 0 C. The resulting mixture was stirred at room temperature overnight. The mixture was poured into a sat. a^SO, aqueous solut ion (30 ml ). The mixture was extracted by dichloromethane (50 mL x 2 ). Then the organic phase was washed with a sat. aHCO; aqueous solution ( 50 mL ) and brine (50 mL ). The organic layer was dried ov er anhydrous Na2S04. A white solid precipitated which was filtered to obtain intermediate 505 (6.4 g, 87% yield).
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 19h;	To a solution of <strong>[959121-99-4]3-bromo-7-methoxyquinoline</strong> (2.0 g, 8.40 mmol) in DCM(42 mL) at RT, mCPBA (2.9 g, 16.8 mmol) was added, and the reaction mixture was stirred at RT for 1 hour. A second portion of mCPBA (2.9 g, 16.8 mmol) was then added, and the reaction mixture was stirred at RT for 18 hours. The reaction mixture was poured onto 10% aqueous Na2SO3 and DCM, and the layers were separated. The organic layer was washed with NaHCO3, dried over MgSO4, filtered and concentrated. The resulting product was used with no further purification. LRMS (M+H)+ = 254.2.

	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 25℃; for 19h;	Intermediate CI l : Methyl (4J?)-4-[(7-methoxy-3-vinylquinolin-2-yl)oxyl-L-prolinate hydrochlorideStep 1: 3-Bromo-7-methoxyquinoline 1 -oxideTo a solution of <strong>[959121-99-4]3-bromo-7-methoxyquinoline</strong> (2.0 g, 8.40 mmol) in DCM (42 mL) at RT, mCPBA (2.9 g, 16.8 mmol) was added, and the reaction mixture was stirred at RT for 1 hour. A second portion of mCPBA (2.9 g, 16.8 mmol) was then added, and the reaction mixture was stirred at RT for 18 hours. The reaction mixture was poured onto 10% Na2SO3(aq.) and DCM, and the layers were separated. The organic layer was washed with NaHCO3, dried over MgSO4, filtered and concentrated. The resulting product was used with no further purification. LRMS (M+H)+ = 254.2.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 19h;	mCPBA (2.9 g, 16.8 mmol) was added to a solution of <strong>[959121-99-4]3-bromo-7-methoxyquinoline</strong> (2.0 g, 8.40 mmol) in DCM (42 mL) at RT, and the reaction mixture was stirred at RT for 1 h. A second portion of mCPBA (2.9 g, 16.8 mmol) was then added, and the reaction mixture was stirred at RT for 18 h. The reaction mixture was poured onto 10% aqueous Na2SO3 and DCM, and the layers were separated. The organic layer was washed with NaHCO3, dried over MgSO4, filtered and concentrated. The resulting product was used with no further purification. LRMS (M+H)+ = 254.2.
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 25℃; for 1.5h;	To a solution of <strong>[959121-99-4]3-bromo-7-methoxyquinoline</strong> (1.0 g, 4.2 mmol) in CH2Cl2 (10 mL) was added 3-chlorobenzoyl peroxide (870 mg, 5.06 mmol) portion wise at 0 C. The resulting mixture was stirred at 25 C for 1.5 h. The mixture was poured into a saturated aqueous solution of Na2S2O3 (50 mL). The mixture was extracted with DCM (50 mL × 2). The organic phase was washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and filtered. After partial concentration, a solid precipitated and was filtered to obtain 3-bromo- 7-methoxyquinoline 1-oxide. MS: 254, 256 (M + 1).1H NMR (400 MHz, Chloroform-d) d 8.67 (s, 1H), 8.02 (s, 1H), 7.88 (s, 1H), 7.71 (d, J = 9.0 Hz, 1H), 7.33 (dd, J = 9.1, 2.2 Hz, 1H), 4.03 (s, 3H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7207 - 7213.
[2]Patent: WO2017/32840,2017,A1 .Location in patent: Page/Page column 237.
[3]Patent: WO2008/57208,2008,A2 .Location in patent: Page/Page column 52.
[4]Patent: WO2008/57209,2008,A1 .Location in patent: Page/Page column 56.
[5]Patent: EP2268285,2018,B1 .Location in patent: Paragraph 0172; 0173.
[6]Patent: WO2020/33282,2020,A1 .Location in patent: Page/Page column 50.

2
[ 959121-99-4 ]
[ 10365-98-7 ]
[ 1017860-10-4 ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 2158 - 2169.

3
[ 2065-75-0 ]
[ 536-90-3 ]
[ 959121-99-4 ]

Yield	Reaction Conditions	Operation in experiment
20%		For the synthesis of this starting compound, 1.80 g (12.3 mmol, 1.1 eq) of bromomalondialdehyde was first dissolved in 30 ml of ethanol, and 1.25 ml of m-anisidine was added. This reaction mixture is stirred over night at RT and, after the addition of acetic acid (20 ml), at 100 C. for 10 days. The solvent is subsequently removed in vacuum on a rotary evaporator, and the residual solid is partitioned between a water and an ethyl acetate phase. The aqueous phase is made alkaline with an ammonia solution, and insoluble particles were filtered off. The filtrate is extracted with ethyl acetate, and the organic phase is dried over MgSO4, filtered, and the solvent is removed in vacuum on a rotary evaporator. The product was purified by column chromatography with a mixture of hexane/ethyl acetate 8/2 as the eluent in a yield of 20% (700 mg). C10H8BrNO; MW 237/239; 1H-NMR (CDCl3): delta 8.76 (d, J=2.2 Hz, 1H), 8.15 (d, J=2.2 Hz, 1H), 7.55 (d, J=9.1 Hz, 1H), 7.32 (d, J=2.5 Hz, 1H), 7.15 (dd, J=2.5 Hz, J=8.8 Hz, 1H), 3.88 (s, 3H, OMe); 13C-NMR (CDCl3): delta 159.9, 150.4, 147.1, 135.9, 126.9, 123.4, 119.9, 113.6, 106.3, 54.6; IR: 2961, 1620, 1581, 1491, 1462, 1417, 1261, 1027, 796 1/cm; MS (ESI): 238-240 (M+H)+
3.8%		To a solution of bromo-malonaldehyde (10 g, 66.2 mmol) in absolute ethanol (100 mL) was added 3-methoxyaniline (7.3 g, 59.6 mmol). The mixture was heated to 30 C and stirred at that temperature for 24 h. Cone. HCl (100 mL) was added, and the reaction mixture was heated at 100C for two days. After the mixture was concentrated and the residue was partitioned between ethyl acetate (150 mL) and saturated sodium carbonate (50 mL). The organic phase was washed with brine, dried with anhydrous Na2S04 and concentrated to give a black oil, which was purified by column chromatography (PE/EA = 3/1) to give Intermediate 13 as a brown oil (500 mg, 3.8%). MS (ESI): m/z 237.9 [M+l]+.

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 2158 - 2169.
[2]Patent: US2010/204234,2010,A1 .Location in patent: Page/Page column 12.
[3]Patent: WO2012/83165,2012,A1 .Location in patent: Page/Page column 98.

4
[ 959121-99-4 ]
[ 14047-29-1 ]
[ 1383379-86-9 ]

Yield	Reaction Conditions	Operation in experiment
29.1%		To a mixture of <strong>[959121-99-4]3-bromo-7-methoxyquinoline</strong> (Intermediate 13, 380 mg, 1.6 mmol), 4-boronobenzoic acid (266 mg, 1.6 mmol) and Na2C03 (848 mg, 8.0 mmol) in DME/H20/EtOH (5 mL, V/V/V = 1/1/0.5) was added Pd(dppf)Cl2 (585 mg, 0.8 mmol). The mixture was heated to 120C by microwave for 1 h. The mixture was partitioned between water (20 mL) and ethyl acetate (20 mL). The aqueous phase was separated and acidified to pH = 3 with 1 N HC1. The precipitate was filtered and dried in vacuo to afford product as a powder (130 mg, 29.1%).

References: [1]Patent: WO2012/83165,2012,A1 .Location in patent: Page/Page column 85.

5
[ 959121-99-4 ]
[ 14047-29-1 ]
[ 1383379-65-4 ]

References: [1]Patent: WO2012/83165,2012,A1 .

6
[ 959121-99-4 ]
[ 1025369-78-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7207 - 7213.
[2]Patent: EP2268285,2018,B1 .

7
[ 959121-99-4 ]
C₃₆H₄₇N₃O₇ [ No CAS ]