2-Fluoropyridine-4-boronic acid synthesis
- Product Name:2-Fluoropyridine-4-boronic acid
- CAS Number:401815-98-3
- Molecular formula:C5H5BFNO2
- Molecular Weight:140.91
5419-55-6
370 suppliers
$12.00/5g
128071-98-7
282 suppliers
$7.00/1g
401815-98-3
243 suppliers
$10.00/250mg
Yield:401815-98-3 91%
Reaction Conditions:
with n-butyllithium in tetrahydrofuran;hexane;toluene at -78; for 1 h;Inert atmosphere;
Steps:
A.1
[00178] Step 1 : To a solution of anhydrous toluene and tetrahydrofuran ("THF") (4:1, 250 mL) were added 4-bromo-2-fluoropyridine 1 (30.0 g, 0.17 mol) and triisopropyl borate (38.4 g, 0.20 mol). The mixture was cooled to -78 °C under a nitrogen atmosphere. Then, n- butyllithium (80 mL, 0.20 mol) (2.5 M in hexanes) was added dropwise over 30 minutes, followed by stirring at the same temperature for an additional 30 minutes. The mixture was finally warmed up to -20 °C over 1 hour. Thin layer chromatography ("TLC") (petroleum ether ("PE"):ethyl acetate ("EtOAc") = 1 :1) indicated that the starting material was consumed. The reaction mixture was acidified to a pH of 2 with 3N HCl (50 mL) and then stirred at room temperature for 15 minutes. The mixture was partitioned between EtOAc (150 mL) and water (150 mL). The organic layer was isolated, washed with water, brine, dried over anhydrous MgS04, then filtered and evaporated to provide (2-fluoropyridin-4-yl)boronic acid (22.0 g, 91%) as a solid.
References:
ARRAY BIOPHARMA INC.;GENENTECH, INC.;BLAKE, James, F.;COOK, Adam;GAUDINO, John;GUNAWARDANA, Indrani, W.;HICKEN, Erik, James;HUNT, Kevin, W.;LYON, Michael;METCALF, Andrew, T.;MOHR, Peter, J.;MORENO, David, A.;NEWHOUSE, Brad;REN, Li;SCHWARZ, Jacob;CHEN, Huifen;GAZZARD, Lewis;SCHMIDT, Jane;DO, Steve WO2015/103137, 2015, A1 Location in patent:Paragraph 00178
5419-55-6
370 suppliers
$12.00/5g
22282-70-8
267 suppliers
$8.00/1g
401815-98-3
243 suppliers
$10.00/250mg
128071-98-7
282 suppliers
$7.00/1g
401815-98-3
243 suppliers
$10.00/250mg
688-74-4
320 suppliers
$10.40/25mL
22282-70-8
267 suppliers
$8.00/1g
401815-98-3
243 suppliers
$10.00/250mg