tert-Butyl isocyanate → (5-Bromo-4-methylpyridin-2-yl)-n-t-butyl carboxylic amide

HRID 661606

Reaktionsgleichung

Reaktionsgleichung von HRID 661606
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][N:3]=1.[Li]CCCC.[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1(C)C=CC=CC=1>[Br:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[N:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 62412tert-Butyl isocyanateHCID 27344292,5-Dibromo-4-methylpyridineHCID 178418339Butyllithium

Produkt 1

HCID 68468634(5-Bromo-4-methylpyridin-2-yl)-n-t-butyl carboxylic amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2,5-Dibromo-4-methylpyridine (1.83 g, 7.29 mmol) was dissolved in toluene (100 mL), cooled to −78° C. and a solution of nBuLi (4.4 mL, 8.8 mmol, 2.0 M in pentane) was added dropwise and stirred at −78° C. for 2 h. A solution of tBuNCO (1.1 mL, 9.5 mmol) in toluene (3 mL) was added dropwise and stirred for 1 h at −78° C. then warmed to −10° C. and quenched by addition of NH4Cl (aq). After warming to r.t. the reaction was extracted with ether and the organics dried over Na2SO4 and concentrated. The product was used without further purification. MS [M+H]+: 271.0; tR=2.44 min. (method 1)

Aufarbeitung

  1. stirringstirred for 1 h at −78° C.
  2. temperaturethen warmed to −10° C.
  3. customquenched by addition of NH4Cl (aq)
  4. temperatureAfter warming to r.t. the reaction
  5. extractionwas extracted with ether
  6. dry with materialthe organics dried over Na2SO4
  7. concentrationconcentrated
  8. customThe product was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-fceb5ed9f77045c3b6fb0ee255652505
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084614B2

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