Triethylamine → N-(5-Fluoropyridin-2-yl)pivalamide

HRID 501089

Reaktionsgleichung

Reaktionsgleichung von HRID 501089
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].C([O-])(O)=O.[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])=[N:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 27377012-Amino-5-fluoropyridine

Produkt 1

HCID 22293237N-(5-Fluoropyridin-2-yl)pivalamideAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0° C. solution of 2-amino-5-fluoropyridine (1.00 g, 8.92 mmol) and triethylamine (1.35 g, 13.4 mmol) in dichloromethane (30 mL) was added trimethylacetyl chloride (1.29 g, 10.7 mmol) and DMAP (0.11 g, 0.89 mmol). The solution was allowed to warm to room temperature. After 4 h, saturated aqueous NaHCO3 was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by silica gel chromatography (5%→40% EtOAc/hexanes) to give the title compound (1.34 g). MS 197.3 (M+1).

Aufarbeitung

  1. customthe layers separated
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (5%→40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-727cff607a104e7daa1dd424fd3fe9da
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772224B2

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