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1-(5-Bromo-3-fluoropyridin-2-yl)ethanone synthesis
- Product Name:1-(5-Bromo-3-fluoropyridin-2-yl)ethanone
- CAS Number:1160936-52-6
- Molecular formula:C7H5BrFNO
- Molecular Weight:218.02
![5-BROMO-3-FLUORO-PYRIDINE-2-CARBONITRILE](/StructureFile/ChemBookStructure21/GIF/CB1801798.gif)
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![Methylmagnesium chloride](/CAS/GIF/676-58-4.gif)
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Yield: 93%
Reaction Conditions:
Stage #1:5-bromo-3-fluoropyridine-2-carbonitrile;methylmagnesium chloride in tetrahydrofuran at 0; for 0.25 h;Inert atmosphere;
Stage #2: with hydrogenchloride;water in tetrahydrofuran at 0 - 20; for 16 h;Inert atmosphere;
Steps:
1.1 Example 1: Preparation of Compound 20
Step 1: To an oven-dried round bottom flask was added 5-bromo-3-fluoro-pyridine-2- carbonitrile (10.1 g, 50.0 mmol), which was cycled under nitrogen. THF (250 mL) was added and the stirred solution was cooled to 0 °C. MeMgCl (3.0 M, 16.75 mL) was added dropwise and the mixture stirred at 0 °C for 15 minutes. The cold reaction mixture was cannulated into a stirring solution of HCl (aqueous, 3 M, 500 mL) also at 0 °C. After addition, the mixture was warmed to room temperature and stirred for 16 hours. The solution was then reverse quenched by addition to a saturated aqueous sodium carbonate solution at 0 °C. The aqueous layer was extracted with ethyl acetate (2 x 500 mL). The organic layers were combined, dried over Na2SO4 and concentrated to afford 1-(5-bromo-3-fluoro-2-pyridyl)ethanone (10.1 g, 93%) as a solid. MS m/z 219.0 [M+H]+.
References:
PTC THERAPEUTICS, INC.;SYDORENKO, Nadiya;ALAM, Md Rauful;AMEDZO, Lukiana;ARNOLD, Michael A.;BABU, Suresh;BHATTACHARYYA, Anuradha;KARP, Gary Mitchell;KENTON, Nathaniel T.;LUONG, Tom Tuan;MAZZOTTI, Anthony R.;MOON, Young-Choon;MORRILL, Christie;MSZAR, Nicholas Walter;NARASIMHAN, Jana;PATEL, Jigar S.;REN, Hongyu;TURPOFF, Anthony;WANG, Gang;WOLL, Matthew G.;ZHANG, Nanjing;ZHANG, Xiaoyan WO2020/231977, 2020, A1 Location in patent:Page/Page column 189-190
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162 suppliers
$8.00/250mg
![1-(5-Bromo-3-fluoropyridin-2-yl)ethanone](/CAS/GIF/1160936-52-6.gif)
1160936-52-6
64 suppliers
$75.00/25mg