Water → Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamate

HRID 1894814Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894814
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][NH2:15])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1.CN(C1C=CC=CN=1)C.[C:25](OC([O-])=O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].O>ClCCl.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][NH:15][C:25](=[O:26])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 218852-DimethylaminopyridineHCID 22064466Tert-butyldicarbonateHCID 66591283[3-(5-Bromopyrid-2-yl)phenyl]methylamine

Produkt 1

HCID 86664991Tert-butyl[3-(5-bromopyrid-2-yl)phenyl]methylcarbamateAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1.07 g (4 mmol, 1 eq) of [3-(5-bromopyrid-2-yl)phenyl]methylamine are dissolved in 10 mL of dichloromethane in the presence of 1 mL of triethylamine and 200 mg of dimethylaminopyridine. 1.7 g (8 mmol, 2 eq) of tert-butyl dicarbonate are added and the reaction mixture is stirred overnight at 40° C. The reaction is stopped by adding 30 ml of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate). 1.18 g of tert-butyl [3-(5-bromopyrid-2-yl)phenyl}methylcarbamate are obtained. Yield=81%.

Aufarbeitung

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (70/30 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-0f1c5a6d494641f4b47e59853f2ace56
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513297B2

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