Sodium Azide → 4-Azidomethyl-2-bromo-6-methyl-pyridine

HRID 1361209Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361209
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]OS(C)(=O)=O)[CH:5]=[C:4]([CH3:14])[N:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:8][C:6]1[CH:5]=[C:4]([CH3:14])[N:3]=[C:2]([Br:1])[CH:7]=1)=[N+:16]=[N-:17]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 59278256Methanesulfonic acid 2-bromo-6-methyl-pyridin-4-ylmethyl ester

Produkt 1

HCID 592785094-Azidomethyl-2-bromo-6-methyl-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methanesulfonic acid 2-bromo-6-methyl-pyridin-4-ylmethyl ester (410 mg, 1.46 mmol) in DMF (2.0 mL) was added sodium azide (238 mg, 3.66 mmol). After 15 hours, the reaction was quenched with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was passed through a pad of silica gel eluting with 30% ethyl acetate in heptane to afford 4-azidomethyl-2-bromo-6-methyl-pyridine.

Aufarbeitung

  1. customthe reaction was quenched with water (10 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1650ee17d0b14a039ec131372baa2124
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879873B2

Notizen zur Reaktion

Wird geladen…