[ CAS No. 880870-66-6 ] {[proInfo.proName]}

Name: 880870-66-6|5-Bromo-2-fluoro-3-methoxypyridine|98%
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SKU: A566760
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Quality Control of [ 880870-66-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 880870-66-6 ]

CAS No. :	880870-66-6	MDL No. :	MFCD09909847
Formula :	C₆H₅BrFNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KWAGWMGOGGVRHV-UHFFFAOYSA-N
M.W :	206.01	Pubchem ID :	58626691
Synonyms :

Safety of [ 880870-66-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 880870-66-6 ]

* 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 [ 880870-66-6 ]

[ 880870-66-6 ] Synthesis Path-Downstream 1~24

1
[ 152684-26-9 ]
[ 880870-66-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at 70℃; for 15.0h;	The compound (21.97 g, 94.28 mmol) obtained in Step 2 was dissolved in dimethylformamide (190 ml), 1 M tetrabutylammonium fluoride tetrahydrofuran solution (190 ml, 0.19 mol) was added, and the mixture was stirred with heating at 70 C. for 15 hr. The reaction mixture was added to water, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1) to give the object product as a white solid (12.21 g, yield 63%). 1H NMR(CDCl3 400 MHz) (delta) ppm: 3.92 (3H, s), 7.40 (1H, dd, J=8.6, 2.1 Hz), 7.81 (1H, dd, J=2.0, 1.0 Hz)
		Example 327Synthesis of (1R,2S)-2-[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(6-fluoro-5-methoxypyridin-3-yl)-2-phenylcyclopropanecarboxamide (327)(1) Synthesis of 3-bromo-6-fluoro-5-methoxypyridine (327-1)Tetrabutyl ammonium fluoride (1.0 M THF solution: 3.9 ml) was added to a DMF (5 ml) solution of <strong>[152684-26-9]5-bromo-3-methoxy-2-nitropyridine</strong> (CAS No. 152684-26-9) (450 mg), and the obtained mixture was stirred at 70 C. for 72 hours. The reaction solution was cooled to room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=10:1 to 2:1), so as to obtain the title compound (258 mg).1H-NMR (400 MHz, CDCl3) 5 (ppm): 3.91 (s, 3H), 7.39 (dd, J=8.8, 2.4 Hz, 1H), 7.80 (t, J=2.4 Hz, 1H).

Reference： [1]Patent: US2006/84665,2006,A1 .Location in patent: Page/Page column 70
[2]Patent: US2012/95031,2012,A1 .Location in patent: Page/Page column 162

2
[ 869893-91-4 ]
[ 880870-66-6 ]
[ 880870-67-7 ]

Yield	Reaction Conditions	Operation in experiment
79%		Under an argon atmosphere, 1M 3-chloro-2-fluorobenzylzinc bromide tetrahydrofuran solution (70.00 ml, 70.00 mmol) was added dropwise to dichlorobistriphenylphosphine palladium (II) (2.00 g, 2.95 mmol), and the mixture was stirred at room temperature for 5 min. Then, a solution of the compound (12.21 g, 59.27 mmol) obtained in Step 3 in tetrahydrofuran (120 ml) was added dropwise, and the mixture was stirred with heating at 60 C. for 1 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, saturated aqueous sodium hydrogencarbonate solution (twice) and saturated brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1 to 4:1) to give the object product as a white solid (12.57 g, yield 79%). 1H NMR(CDCl3 400 MHz) (delta) ppm: 3.87 (3H, s), 3.99 (2H, s), 7.02-7.07 (2H, m), 7.10 (1H, dd, J=9.7, 1.9 Hz), 7.28-7.33 (1H, m), 7.62-7.63 (1H, m)

Reference： [1]Patent: US2006/84665,2006,A1 .Location in patent: Page/Page column 70

3
[ 880870-66-6 ]
[ 1369768-75-1 ]
[ 1369766-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium triphosphate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 15h;	(2) Synthesis of (1R,2S)-2-[(2,4-dimethylpyrimidin-5-yl)oxy]methyl}-N-(6-fluoro-5-methoxypyridin-3-yl)-2-phenylcyclopropanecarboxamide (327)A 1,4-dioxane (3 ml) solution of the carboxamide73-1 (50 mg), the compound 327-1 (48 mg), xantphos (29 mg), potassium triphosphate (71 mg) and Pd2DBA3 (15 mg) was heated to 100 C. and stirred for 15 hours. Water was added to the reaction solution, and the obtained mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane to n-heptane:ethyl acetate=1:2), so as to obtain the title compound (5.9 mg).1H-NMR (400 MHz, CDCl3) delta (ppm): 1.65 (dd, J=8.0, 5.6 Hz, 1H), 1.91 (t, J=5.6 Hz, 1H), 2.10 (dd, J=8.0, 5.6 Hz, 1H), 2.25 (s, 3H), 2.56 (s, 3H), 3.81 (s, 3H), 4.47 (d, J=9.6 Hz, 1H), 4.54 (d, J=9.6 Hz, 1H), 7.30 (t, J=7.2 Hz, 1H), 7.37 (t, J=7.2 Hz, 2H), 7.46 (d, J=7.2 Hz, 2H), 7.54 (t, J=2.4 Hz, 1H), 7.71 (brs, 1H), 7.93 (dd, J=9.2, 2.4 Hz, 1H), 8.01 (s, 1H).MS [M+Na]+=423

Reference： [1]Patent: US2012/95031,2012,A1 .Location in patent: Page/Page column 162

4
[ 880870-66-6 ]
[ 73183-34-3 ]
(6-fluoro-5-methoxypyridin-3-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 83℃;Inert atmosphere;	To a mixture of 4,4,4,4,5,5,5 ?,5?-octamethyl-2,2?-bi( 1 ,3,2-dioxaborolane) (2.4659.71 mmol), potassium acetate (1.429 g, 14.56 mmol) and <strong>[880870-66-6]5-bromo-2-fluoro-3-methoxypyridine</strong> (1 g, 4.85 mmol) in 1,4-dioxane (15 mL) was added 1,1?- bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (0.355 g, 0.485 mmol). The mixture was stirred overnight at 83 C under the nitrogen. Then, the reaction mixture was taken up in. EtOAc (300 ml) and H20 (150 mL). Organic layer wasseparated and washed with H20 (lOOmL x 3), dried with Na2SO4 and concentrated. The residue was purified by silica gel column (Pet. ether/EtOAc 3:1) to afford the desired product (6-fluoro-5-methoxypyridin-3-yl)boronic acid (0.67 g, 76 % yield). LCMS [M + Hj = 172.1.

Reference： [1]Patent: WO2018/127800,2018,A1 .Location in patent: Page/Page column 149; 150

5
[ 880870-66-6 ]
(S)-isopropyl 2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-6’-fluoro-5‘-methoxy-6-methyl-[3,3‘-bipyridin]-5-yl)acetate [ No CAS ]

Reference： [1]Patent: WO2018/127800,2018,A1

6
[ 880870-66-6 ]
(S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-1-yl)-6’-isobutoxy-5‘-methoxy-6-methyl[3,3‘-bipyridin]-5-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2018/127800,2018,A1

7
[ 880870-66-6 ]
[ 97674-02-7 ]
1-(6-fluoro-5-methoxypyridin-3-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.4%		To a solution of <strong>[880870-66-6]5-bromo-2-fluoro-3-methoxypyridine</strong> (25 g, 121 .35 mmol) in toluene (250.0 mL) was added Pd(PPh3)4 (9.82 g, 8.49 mmol) and tributyl(1- ethoxyvinyl)stannane (65.74 g, 182.03 mmol). The mixture was stirred at 100 C for 16 hrs. The mixture was concentrated and to the residue was added aq.HCI (0.5 M, 200 mL) and THF (200 mL). The mixture was stirred at 15-20 C for 1 hr. The mixture was adjusted to pH 8 by adding NaHCO3. Then saturated KF (200mL) was added. The solution was stirred at 15C for 1 hr. The mixture was extracted with EA (200 ml x3). The combined organic layers were dried concentrated and purified by column chromatography (9~16% of ethyl aceate in Hexane) to 1- (6-fluoro-5-methoxypyridin-3-yl)ethan-1-one (G7-1) (16.7 g, 81.4 % yield) as a white solid. 1H NMR (CDCI3, 400MHz):d ppm 8.33 (d, J= 1 .5 Hz, 1 H), 7.83 (dd, J= 1 .6, 9.7 Hz, 1 H), 3.96 (d, J=1.0 Hz, 3H), 2.63 (d, J=1.1 Hz, 3H). LCMS: MS (ESI) m/z 170.1 [M+H]+.

Reference： [1]Patent: WO2021/28806,2021,A1 .Location in patent: Page/Page column 94

8
[ 880870-66-6 ]
(S)-2-(1-(6-fluoro-5-methoxypyridin-3-yl)ethyl)-7-((2-(methylamino)-1H-imidazol-1-yl)methyl)-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]