Alternatived Products of [ 45673-79-8 ]
Product Details of [ 45673-79-8 ]
CAS No. : | 45673-79-8 |
MDL No. : | MFCD12828023 |
Formula : |
C6H6FNO
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
127.12
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 45673-79-8 ]
Signal Word: | |
Class: | N/A |
Precautionary Statements: | |
UN#: | N/A |
Hazard Statements: | |
Packing Group: | N/A |
Application In Synthesis of [ 45673-79-8 ]
* 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.
- Upstream synthesis route of [ 45673-79-8 ]
- Downstream synthetic route of [ 45673-79-8 ]
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[ 31181-53-0 ]
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[ 45673-79-8 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With 3-chloro-benzenecarboperoxoic acid; |
Example 151 Synthesis of <strong>[31181-53-0]5-fluoro-2-methylpyridine</strong> 1-oxide. To a stirred solution of <strong>[31181-53-0]5-fluoro-2-methylpyridine</strong> (5 g, 45 mmol) in DCM (100 mL) was added m-CPBA (11.6 g, 67.5 mmol) at 0 C. and the mixture was stirred at 25 C. for 16 h. The mixture was quenched with saturated aqueous Na2S2O3, stirred vigorously for 15 min, and then poured into saturated aqueous NaHCO3. The layers were separated, and the aqueous layer was extracted twice more with DCM. The combined organic layers were dried over MgSO4, filtered and concentrated to give <strong>[31181-53-0]5-fluoro-2-methylpyridine</strong> 1-oxide (4.7 g, 82%) as a yellow solid which was used into next step without further purification. ESI-MS [M+H]+: 128.2. |
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With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 16h; |
The preparation was based on E. J. Blanz, F. A. French, J. R. DoAmaral and D. A. French, J. Med. Chem. 13, 1970,1124-1130. 5-Amino-2-picoline (12.5 g) in ethanol (105 ml) and 50% fluoroboric acid (44.5 ml) was stirred at-5C and treated dropwise over 45 minutes. with n-butyl nitrite (31.25 ml). The solution was maintained at this temp. for 3 hours, treated with ether (100 ml, precooled to-20C) and the solid filtered off, quickly transferred to a flask and covered with hexane (precooled to-20C). After allowing to warm to approx. 20C and standing for 3 days the hexane was decanted and 2M NaOH solution added until basic (pH 10). The mixture was filtered and the filtrate extracted with dichloromethane (10 x 200 ml). The organic solution was dried, evaporated to 200 ml and treated with m-chloroperbenzoic acid (26.5 g). After stirring 16 hours the solution was washed with excess aqueous sodium bicarbonate and the aqueous re-extracted with dichloromethane (10 x 200 ml). The organic fraction was dried and evaporated and the residue chromatographed (15% EtOH/EtOAc) to give the pyridine N-oxide (5. 5g). MS (APC) mlz 128 (MH+, 100%) |
220 g |
With 3-chloro-benzenecarboperoxoic acid; at 20℃;Inert atmosphere; |
To a 10-L 4-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was added the solution of <strong>[31181-53-0]5-fluoro-2-methylpyridine</strong> from Step 1 and m-CPBA (671 g, 3.89 mol, 1.20 equiv) in portions. The resulting solution was stirred at room temperature overnight. The pH value of the solution was adjusted to 1 1 -12 with sodium hydroxide (2 N). The resulting solution was extracted with 6x1 L of dichloromethane. The combined organic layers were washed with 1x500 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 220 g (53 %> over two steps) of <strong>[31181-53-0]5-fluoro-2-methylpyridine</strong> 1 -oxide as a yellow solid. |
Reference:
[1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 37 - 41
[2]Patent: US2019/284182,2019,A1
[3]Journal of Medicinal Chemistry,1989,vol. 32,p. 1970 - 1977
[4]Patent: WO2003/87098,2003,A1 .Location in patent: Page/Page column 95-96
[5]Tetrahedron Letters,2010,vol. 51,p. 5035 - 5037
[6]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4824 - 4827
[7]Patent: WO2018/15410,2018,A1 .Location in patent: Paragraph 0365; 0369-0371
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[ 45673-79-8 ]
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[ 113209-90-8 ]
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