Triethylamine → N-(6-methoxypyridin-3-yl)pivalamide

HRID 2384488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384488
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.CCN(CC)CC.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 811216-Methoxy-3-pyridinylamine

Produkt 1

HCID 5323848N-(6-methoxypyridin-3-yl)pivalamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 6-methoxy-pyridin-3-amine (Aldrich, 10.0 g, 77 mmol) in anhydrous CH2Cl2 (100 ml) at 0° C. was added Et3N (13.9 ml, 100.1 mmol) and a solution of pivaloyl chloride (10.5 ml, 84.7 mmol) in CH2Cl2 (20 ml). The mixture was stirred at 0° C. for 10 min and at room temperature for 2 h. After quenched with ice, the reaction was diluted with CH2Cl2, washed with 1M NaOH, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as orange solid.

Aufarbeitung

  1. customAfter quenched with ice
  2. additionthe reaction was diluted with CH2Cl2
  3. washwashed with 1M NaOH, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e7e37e28adaa4607bc752b88c61b8fa9
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263767B2

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