5-Bromo-2-methoxypyridine-3-carbaldehyde → HCID 58941096, Verbindung

HRID 506867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506867
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31]P(=O)(OCC)OCC)=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CC(C)([O-])C.[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:31]/[C:28]2[CH:27]=[CH:26][C:25]([N:22]3[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:24][CH2:23]3)=[CH:30][CH:29]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 15164035-Bromo-2-methoxypyridine-3-carbaldehydeHCID 23665647Potassium tert-butoxideHCID 58941093HCID 58941093, Verbindung

Produkt 1

HCID 58941096HCID 58941096, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 5-bromo-2-methoxypyridine-3-carbaldehyde (1.5 g, 6.95 mmol) and diethyl (4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl)methylphosphonate (2.39 g, 5.79 mmol) in anhydrous THF (50 mL) under nitrogen was added potassium tert-butoxide (1.30 g, 11.6 mmol) at rt over 5 min. After 3 h a further portion of the aldehyde (160 mg, 0.74 mmol) was added. After a further 30 min the reaction was concentrated and the residue purified by column chromatography (30% EtOAc in PE) to give the title compound (2.27 g, 83%) as a yellow oil. 1H NMR (CDCl3) 1.51 (9H, s), 3.24 (4H, t), 3.68 (4H, t), 4.00 (3H, s), 7.02 (2H, d), 7.11 (2H, m), 7.49 (2H, d), 7.89 (1H, s), 8.07 (1H, s).

Aufarbeitung

  1. concentrationAfter a further 30 min the reaction was concentrated
  2. customthe residue purified by column chromatography (30% EtOAc in PE)

Quellen und Nachweise

ORD-Eintrag
ord-647c92aebf054ee3a3dd9a8455ef7a9a
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786120B2

Notizen zur Reaktion

Wird geladen…