1-Bromo-3-methylbutane → 6-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione

HRID 1965272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1965272
[S:1]1[C:5]2=[C:6]3[C:10](=[CH:11][CH:12]=[C:4]2[N:3]=[CH:2]1)[NH:9][C:8](=[O:13])[C:7]3=[O:14].O1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30]>CN(C)C=O>[CH3:30][CH:29]([CH3:31])[CH2:28][CH2:27][N:9]1[C:10]2[C:6](=[C:5]3[S:1][CH:2]=[N:3][C:4]3=[CH:12][CH:11]=2)[C:7](=[O:14])[C:8]1=[O:13]

Komponenten

6

Edukt 4

HCID 78911-Bromo-3-methylbutaneHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 117457566H-thiazolo[5,4-e]indole-7,8-dione

Produkt 1

HCID 673588366-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dioneAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 6H-thiazolo[5,4-e]indole-7,8-dione (2.83 g, 13.9 mmol) in a mixture of anhydrous tetrahydrofuran (120 mL) and N,N-dimethylformamide (80 mL) was added cesium carbonate (23.0 g, 70 mmol) at ambient temperature. The deep purple mixture was stirred for 0.5 h followed by the addition of 1-bromo-3-methylbutane (4.15 mL, 35.0 mmol) in one portion. The mixture was stirred at ambient temperature for 16 h and poured into 800 mL of ice-water and extracted with ethyl acetate. The orange solution was filtered through Celite, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to dryness and the residue was triturated with diethyl ether to afford 6-(3-methylbutyl)-6H-[1,3]thiazolo[5,4-e]indole-7,8-dione (2.2 g, 57%): 1H NMR (300 MHz, CDCl3) δ9.36 (s, 1H), 8.38 (d, J=8.6 Hz, 1H), 7.37 (d, J=8.6 Hz, 1H), 3.77-3.69 (m, 2H), 1.74-1.58 (m, 1H), 1.57-1.47 (m, 2H), 0.94 (d, J=6.5 Hz, 6H).

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 16 h
  2. extractionextracted with ethyl acetate
  3. filtrationThe orange solution was filtered through Celite
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness
  7. customthe residue was triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3dc42295abc6497ea5d20cbfb8488eea
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415370B2

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