ChemicalBook CAS DataBase List 1-(5-Bromo-3-fluoropyridin-2-yl)ethanone

1-(5-Bromo-3-fluoropyridin-2-yl)ethanone synthesis

6synthesis methods

Product Name:1-(5-Bromo-3-fluoropyridin-2-yl)ethanone
CAS Number:1160936-52-6
Molecular formula:C7H5BrFNO
Molecular Weight:218.02

886373-28-0 Synthesis

5-Bromo-3-fluoro-pyridine-2-carbonitrile

886373-28-0
165 suppliers
$8.00/250mg

676-58-4 Synthesis

676-58-4
297 suppliers
$15.00/25ml

1-(5-Bromo-3-fluoropyridin-2-yl)ethanone

1160936-52-6
68 suppliers
$75.00/25mg

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 Na₂SO₄and 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