tert-Butanol → Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

HRID 1172425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172425
[Br:1][C:2]1[CH:7]=[C:6](C(O)=O)[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1.C([N:17]([CH2:20]C)CC)C.[C:22]([OH:26])([CH3:25])([CH3:24])[CH3:23].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1>O.O1CCOCC1>[Br:1][C:2]1[CH:7]=[C:6]([NH:17][C:20]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:34])[N:5]=[C:4]([C:11]([O:13][CH3:14])=[O:12])[CH:3]=1

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 469414564-Bromo-6-(methoxycarbonyl)pyridine-2-carboxylic acid

Produkt 1

HCID 25067269Methyl 4-bromo-6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of 4.62 g of methyl hydrogen 4-bromopyridine-2,6-dicarboxylate, 2.97 ml of triethylamine, 25 ml of t-butanol and 70 ml of 1,4-dioxane was added 4.59 ml of diphenylphosphoryl azide at room temperature. The reaction mixture was heated under reflux for 3 hours and cooled to room temperature. Water was added thereto and the resulting mixture was extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe obtained ethyl acetate solution was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7fd21717c6d14f91a36b46b34fec5178
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834018B2

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