Potassium Carbonate → 1-(3-fluorobenzyl)-4-[(4-fluorobenzyl)oxy]-3-iodopyridin-2(1H)-one

HRID 1867024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867024
[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([I:13])[C:7]1=[O:14].C([O-])([O-])=O.[K+].[K+].[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][N:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:29][C:28]2[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=2)=[C:8]([I:13])[C:7]1=[O:14]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 54724182HCID 54724182, Verbindung

Produkt 1

HCID 101515901-(3-fluorobenzyl)-4-[(4-fluorobenzyl)oxy]-3-iodopyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 1-(3-fluorobenzyl)-4-hydroxy-3-iodopyridin-2(1H)-one (0.5 g, 1.44 mmol) in DMF (5 mL) was added K2CO3 (0.199 g, 1.44 mmol) followed by the addition of 4-fluorobenzyl bromide (0.189 mL, 1.51 mmol). The reaction mixture stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate (50 mL) and washed with water. The organic extracts were dried over anhydrous Na2SO4 and concentrated to dryness. 1H-NMR (CD30), 400 MHz) δ7.75 (d, 1H, J=7.6 Hz), 7.49 (q, 2H), 7.34 (q, 1H), 7.11 (m, 5H), 6.40 (d, 1H, J=7.6 Hz), 5.26 (s, 2H), 5.19 (s, 2H); ES-HRMS m/z 454.0098 (M+H calculated for C19H15NO2F2I requires 454.0110).

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  3. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-7a1bb7a1546848dc806003749fb022f1
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07629363B2

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