Water → 2-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester

HRID 245079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 245079
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6](Cl)[CH:5]=1.[Br-].[CH3:15][CH2:16][CH:17]([Zn+])[CH2:18][CH3:19].O>C1COCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:6]([CH:17]([CH2:18][CH3:19])[CH2:16][CH3:15])[CH:5]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 13339618Methyl 2-chloro-6-methoxyisonicotinateHCID 178456109HCID 178456109, Verbindung

Produkt 1

HCID 670268752-(1-Ethylpropyl)-6-methoxyisonicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Under argon, Pd(dppf) (3.04 g, 4 mmol) is added to a solution of 2-chloro-6-methoxy-isonicotinic acid methyl ester (50 g, 0.248 mol) in THF (100 mL). A 0.5 M solution of 3-pentylzincbromide in THF (550 mL) is added via dropping funnel. Upon complete addition, the mixture is heated to 85° C. for 18 h before it is cooled to rt. Water (5 mL) is added and the mixture is concentrated. The crude product is purified by filtration over silica gel (350 g) using heptane:EA 7:3 to give 2-(1-ethyl-propyl)-6-methoxy-isonicotinic acid methyl ester (53 g) as a pale yellow oil; 1H NMR (CDCl3): δ0.79 (t, J=7.5 Hz, 6H), 1.63-1.81 (m, 4H), 2.47-2.56 (m, 1H), 3.94 (s, 3H), 3.96 (s, 3H), 7.12 (d, J=1.0 Hz, 1H), 7.23 (d, J=1.0 Hz, 1H).

Aufarbeitung

  1. additionUpon complete addition
  2. temperatureis cooled to rt
  3. concentrationthe mixture is concentrated
  4. filtrationThe crude product is purified by filtration over silica gel (350 g)

Quellen und Nachweise

ORD-Eintrag
ord-6afaebd5f60645648aa23aa8fecedf76
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658675B2

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