Sodium hydride → N-[4-(4-bromo-6-methyl-pyridin-3-yloxymethyl)-thiazol-2-yl]-acetamide

HRID 1807689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807689
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=1[OH:9].[H-].[Na+].[C:12]([NH:15][C:16]1[S:17][CH:18]=[C:19]([CH2:21]Cl)[N:20]=1)(=[O:14])[CH3:13]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[CH:4][C:3]=1[O:9][CH2:21][C:19]1[N:20]=[C:16]([NH:15][C:12](=[O:14])[CH3:13])[S:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 819632-Acetamido-4-chloromethylthiazoleHCID 580927194-Bromo-6-methylpyridin-3-ol

Produkt 1

HCID 86649535N-[4-(4-bromo-6-methyl-pyridin-3-yloxymethyl)-thiazol-2-yl]-acetamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 270 mg (1.44 mmol) 4-bromo-6-methyl-pyridin-3-ol (Stage 40.4) in DMF (5 mL), 44.8 mg NaH (1.87 mmol) was added and this mixture was stirred for 1 h at rt. 301 mg (1.58 mmol) 2-acetamido-4-(chloromethyl)-1,3-thiazole (Apollo OR15549) was added and stirring was continued at rt for another 17 h. The reaction mixture was poured on water and extracted with EtOAc (2×). The combined organic layers were washed with water and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to leave 350 mg of the title compound (white solid) considered sufficiently pure without further purification. LCMS: tR=1.36 min, M+H=342 (79Br), 344 (81Br) (method J).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at rt for another 17 h
  3. additionThe reaction mixture was poured on water
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-63bbd180ca614cc99ad07a7085ed685f
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357707B2

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