N-Iodosuccinimide → 4-(benzyloxy)-1-(3-fluorobenzyl)-3-methylpyridin-2(1H)-one

HRID 1832014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1832014
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IN1C(=O)CC[C:26]1=O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[C:10]=1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

Produkt 1

HCID 220499144-(benzyloxy)-1-(3-fluorobenzyl)-3-methylpyridin-2(1H)-oneAusbeute 121,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 4-(benzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one (4.83 g, 15.6 mmol) and N-iodosuccinimide (NIS, 3.86 g, 17.1 mmol) in anhydrous acetonitrile (55 mL) was heated at 65° C. for 4 hours under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (ethyl acetate/hexane 1:1 v/v). The appropriate fractions were collected according to ES MS (M+H 436) and washed with Na2SO3 to remove the color impurities. The fractions were concentrated under reduced pressure and dried in vacuo to afford the desired product (6.15 g, 90%) as a light yellow solid. 1H-NMR (CD3OD, 400 MHz) δ 7.73 (d, 1H, J=7.6 Hz), 7.36 (m, 6H), 7.08 (m, 3H), 6.39 (d, 1H, J=8.0 Hz), 5.28 (s, 2H), 5.19 (s, 2H); ES-HRMS m/z 436.0196 (M+H calculated for C19H16NO2FI requires 436.0210). Step 2. Preparation of 4-(benzyloxy)-1-(3-fluorobenzyl)-3-methylpyridin-2(1H)-one

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (ethyl acetate/hexane 1:1 v/v)
  3. customThe appropriate fractions were collected
  4. washwashed with Na2SO3
  5. customto remove the color impurities
  6. concentrationThe fractions were concentrated under reduced pressure
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-402e45a7e62f4457ac639de075b9c99b
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067540B2

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