Sodium Azide → 5-(Azidomethyl)isoquinoline

HRID 1861674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1861674
Cl[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.CCOC(C)=O>[N:13]([CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2)=[N+:14]=[N-:15]

Komponenten

5

Edukt 2

HCID 33557Sodium Azide2×HCID 120186945-(Chloromethyl)isoquinoline

Produkt 1

HCID 120186955-(Azidomethyl)isoquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.0415 g (0.23 mmol) 16 in 3 mL DMF was added 0.0169 g (0.26 mmol) sodium azide. After a 3 h, an additional 0.0033g (0.05 mmol) portion of sodium azide was added. After 24 h at room temperature, the reaction mixture was diluted with 50 mL EtOAc and washed with 20 mL brine. The aqueous layer was extracted with 10 mL EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (10×175 mm silica gel, linear gradient 5-20% EtOAc:hexane) produced 17. 1H NMR (CDCl3, 400 MHz) δ 9.318 (s, 1H, ArH); 8.637 (d, 1H, J=6.10 Hz, ArH); 8.010 (d, 1H, J=7.94 Hz, ArH); 7.822 (d, 1H, J=6.10 Hz, ArH); 7.713 (d, 1H, J=7.02 Hz, ArH); 7.617 (dd, 1H, J=7.17, 8.09 Hz, ArH); 4.774 (s, 1H, ArH); MS (Electrospray): m/z 185.0 (M+H).

Aufarbeitung

  1. waitAfter 24 h at room temperature
  2. washwashed with 20 mL brine
  3. extractionThe aqueous layer was extracted with 10 mL EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (10×175 mm silica gel, linear gradient 5-20% EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8532594578b346208285051fece14f70
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534510B2

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