2-Bromo-6-fluoropyridine → tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate

HRID 57877

Reaktionsgleichung

Reaktionsgleichung von HRID 57877
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[CH3:9][CH:10]1[NH:15][CH2:14][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]1>CS(C)=O>[Br:1][C:2]1[N:3]=[C:4]([N:15]2[CH:10]([CH3:9])[CH2:11][CH2:12][CH:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6394382-Bromo-6-fluoropyridineHCID 42609251tert-butyl N-(6-methylpiperidin-3-yl)carbamate

Produkt 1

HCID 86707072tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A solution containing 2-bromo-6-fluoropyridine (0.95 mL, 6.65 mmol and tert-butyl 6-methylpiperidin-3-ylcarbamate (750 mg, 3.32 mmol) in methyl sulfoxide 5.0 ml was heated 95° C. 18 h. The reaction was quenched with water then extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was purified by flash chromatography (EtOAc/Heptane eluted at 30% EtOAc) to give tert-butyl N-[1-(6-bromo-2-pyridyl)-6-methyl-3-piperidyl]carbamate (480 mg) in 39% yield. MS (ESI) m/z: 371.2

Aufarbeitung

  1. custom18 h
  2. customThe reaction was quenched with water
  3. extractionthen extracted with EtOAc
  4. dry with materialThe organic layers was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customThe crude product was purified by flash chromatography (EtOAc/Heptane eluted at 30% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-3d401b61bbcc445dbb22ecc949716f4e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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