25759-94-8|4-chloro-7-fluoro-6-methoxyquinoline| Ambeed

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Quality Control of [ 25759-94-8 ] Purity: 98% SDS Specification

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Product Details of [ 25759-94-8 ]

CAS No. :	25759-94-8
Formula :	C₁₀H₇ClFNO
M.W :	211.62
SMILES Code :	COC1=C(F)C=C2N=CC=C(Cl)C2=C1
MDL No. :	MFCD15527286
InChI Key :	VQQKJOIDUVQMPF-UHFFFAOYSA-N
Pubchem ID :	611124

Safety of [ 25759-94-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 25759-94-8 ]

* 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 [ 25759-94-8 ]

[ 25759-94-8 ] Synthesis Path-Downstream 1~28

2
[ 666734-80-1 ]
[ 25759-94-8 ]
3-(7-Fluoro-6-methoxy-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With dmap; caesium carbonate; In dimethyl sulfoxide; at 130℃;	4-Chloro-7-fluoro-6-methoxy-quinoline (50 mg), 5,6-dimethyl-[2,2']bipyridinyl-3-ol (47 mg), and 4-dimethylaminopyridine (87 mg) were dissolved in dimethylsulfoxide (1.5 ml), cesium carbonate (231 mg) was added to the solution, and the mixture was stirred at 130C overnight. The reaction mixture was cooled to room temperature, and water was added thereto. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (47 mg, yield 52%). 1H-NMR (CDCl3, 400 MHz): δ 2.41 (s, 3H), 2.67 (s, 3H), 4.04 (s, 3H), 6.47 (d, J = 5.6 Hz, 1H), 7.11 (ddd, J = 1.0, 4.9, 7.6 Hz, 1H), 7.39 (s, 1H), 7.63 (m, 1H), 7.70 (d, J = 9.0 Hz, 1H), 7.88 - 7.90 (m, 2H), 8.35 (m, 1H), 8.45 (d, J = 5.6 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 398 (M+Na)+

References: [1]Patent: EP1724268,2006,A1 .Location in patent: Page/Page column 74.

3
[ 666735-37-1 ]
[ 25759-94-8 ]
3-(7-Fluoro-6-methoxy-quinolin-4-yloxy)-2-phenyl-[1,8]naphthyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; In 1,2-dichloro-benzene; at 130℃; for 8.0h;	4-Chloro-7-fluoro-6-methoxy-quinoline (50 mg), 2-phenyl-[1,8]naphthyridin-3-ol (53 mg), and 4-dimethylaminopyridine (87 mg) were suspended in 1,2-dichlorobenzene (1.5 ml), and the suspension was stirred at 130C for 8 hr. The reaction mixture was cooled to room temperature, and an aqueous sodium hydrogencarbonate solution was added to the reaction mixture. The organic layer was extracted with chloroform, and the chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography with a methanol-chloroform system to give the title compound (48 mg, yield 50%). 1H-NMR (CDCl3, 400 MHz): δ 4.06 (s, 3H), 6.56 (d, J = 5.4 Hz, 1H), 7.35 - 7.37 (m, 3H), 7.57 (dd, J = 4.1, 8.1 Hz, 1H), 7.65 (d, J = 8.8 Hz, 1H), 7.89 (d, J = 11.0 Hz, 1H), 8.02 (s, 1H), 8.09 (m, 2H), 8.20 (dd, J = 1.7, 8.1 Hz, 1H), 8.52 (d, J = 5.4 Hz, 1H), 9.20 (dd, J = 2.0, 4.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 420 (M+Na)+

References: [1]Patent: EP1724268,2006,A1 .Location in patent: Page/Page column 62.

4
[ 948573-52-2 ]
[ 25759-94-8 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of the material so obtained and phosphorus oxychloride (15 ml) was stirred and heated to 500C for 30 minutes. The excess of phosphorus oxychloride was removed by evaporation and the residue was partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic solution was dried over magnesium sulphate and evaporated. There was thus obtained 4-chloro-7-fluoro-6-methoxyquinoline (1.45 g); 1H NMR: (DMSOd6) 4.06 (s, 3H), 7.6 (d, IH), 7.74 (d, IH)5 7.92 (d, IH), 8.72 (d, IH); Mass Spectrum: M+H+ 212 and 214.
	With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 100℃; for 0.5h;	3-Fluoro-4-methoxyaniline (1.41 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxan-4,6-dione (2.00 g) were suspended in 2-propanol (40 ml), and the mixture was stirred at 70C for 30 min. The reaction mixture was cooled to room temperature, and the precipitated crystal was collected by filtration and was washed with methanol and then with ether. The crystal thus obtained as such was used in the next reaction without further purification. The crystal prepared above and biphenyl (5.8 g) were suspended in diphenyl ether (20 ml), and the suspension was stirred at 220C for one hr. The reaction mixture was cooled to room temperature, and the precipitated crystal was collected by filtration and was washed with chloroform. The crystal thus obtained as such was used in the next reaction without further purification. The residue was suspended in diisopropylethylamine (8 ml), phosphorus oxychloride (2 ml) was added to the suspension, and the mixture was stirred at 100C for 30 min. Water was added to the reaction mixture under ice cooling. The aqueous layer was neutralized with an aqueous sodium hydrogencarbonate solution, and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography with an ethyl acetate hexane system to give 4-chloro-7-fluoro-6-methoxy-quinoline (1.10 g, yield 52%) (3 steps).

References: [1]Patent: WO2007/99326,2007,A1 .Location in patent: Page/Page column 175.
[2]Patent: EP1724268,2006,A1 .Location in patent: Page/Page column 62.

5
[ 25759-94-8 ]
[ 73183-34-3 ]
7-fluoro-6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline [ No CAS ]