Sodium Carbonate → 1-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone

HRID 410272

Reaktionsgleichung

Br[C:2]1[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH:18]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[F:8][C:3]1[C:2]([C:17]2[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH:18]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a round-bottomed flask was added 3-bromo-2-fluoropyridine (0.54 g, 3.1 mmol), 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.96 g, 3.8 mmol), trans-dichlorobis(triphenylphosphine) palladium (II) (0.17 g, 0.25 mmol), and sodium carbonate (0.97 g, 9.2 mmol) in DME (7.5 mL) and Water (2.5 mL). The reaction mixture was stirred at 100° C. for 16 h. After cooling to RT, the reaction mixture was diluted with water (15 mL) and extracted with EtOAc (3×50 mL). The organic extract was washed with water, brine, dried with Na2SO4, filtered, and concentrated. The crude product was chromatographed through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide 1-(4-(2-fluoropyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone (0.14 g, 21% yield) as a yellow oil. MS (ESI, pos. ion) m/z: 221.0 (M+1).

Aufarbeitung

temperatureAfter cooling to RT
extractionextracted with EtOAc (3×50 mL)
extractionThe organic extract
washwas washed with water, brine
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was chromatographed through a Redi-Sep pre-packed silica gel column (40 g)
washeluting with a gradient of 10% to 100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag: ord-e094f56ec2b148ed8c812e576b16d685
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08759532B2

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