Sodium hydride → Ethyl 2-amino-2-(5-bromo-3-chloropyridin-2-yl)acetate

HRID 1502721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502721
C1(C(=[N:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.[H-].[Na+].[Br:23][C:24]1[CH:25]=[C:26]([Cl:31])[C:27](Cl)=[N:28][CH:29]=1>CN(C=O)C>[NH2:14][CH:15]([C:27]1[C:26]([Cl:31])=[CH:25][C:24]([Br:23])=[CH:29][N:28]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 127477605-Bromo-2,3-dichloropyridine

Produkt 1

HCID 71138503Ethyl 2-amino-2-(5-bromo-3-chloropyridin-2-yl)acetateAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Ethyl 2-(diphenylmethyleneamino)acetate (10.2 g, 38.2 mmol) was added to sodium hydride (NaH; 3.18 g, 133.52 mmol) in DMF (50 mL) at 0° C., and the mixture was stirred for 30 min. To this was added 5-bromo-2,3-dichloropyridine (12.9 g, 57.23 mmol), and the reaction mixture was stirred for 3 h at ambient temperature. The reaction mixture was quenched with 2 N HCl solution and then stirred for 4 h at ambient temperature. The mixture was extracted with EtOAc. The combined EtOAc layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (20-30% EtOAc in hexane) afforded the title compound as a liquid (1.3 g, 20%): 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.89 (s, 1H), 5.09 (s 1H), 4.23 (m, 2H), 2.27 (br s, 2H), 1.26 (m, 3H); ESIMS m/z 293.05 ([M+H]+); IR (thin film) 3381, 3306, 1742, 759, 523 cm−1.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 3 h at ambient temperature
  2. customThe reaction mixture was quenched with 2 N HCl solution
  3. stirringstirred for 4 h at ambient temperature
  4. extractionThe mixture was extracted with EtOAc
  5. washThe combined EtOAc layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (20-30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3817ff9b913042a895a6815819368bb2
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09210927B2

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