Sodium borohydride → 6-Bromo-2-chloro-3-(difluoromethoxy)pyridin-4-amine

HRID 407218

Reaktionsgleichung

Reaktionsgleichung von HRID 407218
[N:1]([C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([Cl:11])[C:5]=1[O:12][CH:13]([F:15])[F:14])=[N+]=[N-].[BH4-].[Na+]>CO>[Br:10][C:8]1[N:7]=[C:6]([Cl:11])[C:5]([O:12][CH:13]([F:15])[F:14])=[C:4]([NH2:1])[CH:9]=1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 866754034-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine

Produkt 1

HCID 866754046-Bromo-2-chloro-3-(difluoromethoxy)pyridin-4-amineAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4-Azido-6-bromo-2-chloro-3-(difluoromethoxy)pyridine (0.563 g, 1.880 mmol) was then dissolved in CH3OH (15 mL), and NaBH4 (0.107 g, 2.82 mmol) was added. The reaction mixture was stirred at ambient temperature for 15 min at which point thin-layer chromatographic (TLC) analysis indicated complete consumption of starting material. The reaction mixture was concentrated and partitioned between EtOAc and H2O. The organic phase was dried and concentrated. The product was purified by flash chromatography (SiO2, EtOAc/hexane gradient) to yield the title compound as a white solid (0.398 g, 77%): mp 138-140° C.; 1H NMR (600 MHz, DMSO-d6) δ 6.98 (t, J=73.1 Hz, 1H), 6.84 (d, J=14.6 Hz, 2H); EIMS m/z 274.

Aufarbeitung

  1. customconsumption of starting material
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between EtOAc and H2O
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography (SiO2, EtOAc/hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2f0be027e79b4c5b84b5ffdb7dc6833e
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754229B2

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