Phosphorus oxychloride → tert-Butyl 6-bromo-3',6'-dihydro-2,4'-bipyridine-1'(2'H)-carboxylate

HRID 403198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403198
[Br:1][C:2]1[N:7]=[C:6]([C:8]2(O)[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 86614831tert-Butyl 4-(6-bromopyridin-2-yl)-4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 86614830tert-Butyl 6-bromo-3',6'-dihydro-2,4'-bipyridine-1'(2'H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tert-butyl 4-(6-bromopyridin-2-yl)-4-hydroxypiperidine-1-carboxylate (100 mg) in pyridine (2.5 ml) is added, at 0° C. under argon, POCl3 (0.26 ml). The mixture is stirred at 0° C. and then slowly warmed to room temperature. The mixture is stirred at room temperature overnight. The reaction mixture is subsequently admixed with saturated sodium hydrogencarbonate solution and the aqueous phase is removed. After the aqueous phase has been extracted with tert-butyl methyl ether, the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The residue is purified by chromatography. This gives tert-butyl 6-bromo-3′,6′-dihydro-2,4′-bipyridine-1′(2′H)-carboxylate (60 mg).

Aufarbeitung

  1. temperatureslowly warmed to room temperature
  2. stirringThe mixture is stirred at room temperature overnight
  3. customthe aqueous phase is removed
  4. extractionAfter the aqueous phase has been extracted with tert-butyl methyl ether
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e2d965447b0e49699427a2bb749675df
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748420B2

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