Di-tert-butyl dicarbonate → Tert-butyl(6-bromo-3-methoxypyridin-2-yl)carbamate

HRID 1772885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772885
BrC1N=C(N)C(OC)=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[C:26]([O:30][C:31]([N:33]([C:41]1[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[C:43]([Br:49])[N:42]=1)C(OC(C)(C)C)=O)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C)C1C=CN=CC=1.CC#N>[C:26]([O:30][C:31](=[O:32])[NH:33][C:41]1[C:46]([O:47][CH3:48])=[CH:45][CH:44]=[C:43]([Br:49])[N:42]=1)([CH3:29])([CH3:27])[CH3:28]

Komponenten

6

Edukt 3

HCID 90495Di-tert-butyl dicarbonateHCID 575629062-Amino-6-bromo-3-methoxypyridineHCID 118685198Di-tert-butyl(6-bromo-3-methoxypyridin-2-yl)imidodicarbonate

Produkt 1

HCID 131734688Tert-butyl(6-bromo-3-methoxypyridin-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 6-bromo-3-methoxypyridin-2-amine (10.2 g, 50.2 mmol), Boc2O (38.2 g, 0.18 mol) and 4-(dimethylamino)pyridine (1.2 g, 9.82 mmol) in MeCN (550 mL) was refluxed for 2 h. After cooling to rt and concentration in vacuo EtOAc (500 mL) was added and the organic phase washed with water (100 mL) and brine (50 mL). The organic phase was dried (MgSO4), filtered and the filtrate concentrated in vacuo. Purification by chromatography eluting with 4:1 DCM-heptane yielded a mixture of the title compound and di-tert-butyl(6-bromo-3-methoxypyridin-2-yl)imidodicarbonate (10.6 g) in an approximate ratio of 55:45.

Aufarbeitung

  1. temperaturewas refluxed for 2 h
  2. concentrationconcentration in vacuo EtOAc (500 mL)
  3. additionwas added
  4. washthe organic phase washed with water (100 mL) and brine (50 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification by chromatography
  9. washeluting with 4:1 DCM-heptane
  10. customyielded

Quellen und Nachweise

ORD-Eintrag
ord-0c5f5d9864ed461fa7bcf07e8b4192b3
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249160B2

Notizen zur Reaktion

Wird geladen…