Boron tribromide → 9-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

HRID 1400177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400177
C[O:2][C:3]1[C:4]2[C:5]3[N:16]=[CH:15][S:14][C:6]=3[NH:7][C:8](=[O:13])[C:9]=2[CH:10]=[CH:11][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]2[C:5]3[N:16]=[CH:15][S:14][C:6]=3[NH:7][C:8](=[O:13])[C:9]=2[CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 580160499-methoxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one

Produkt 1

HCID 580160609-Hydroxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-oneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 9-methoxy-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one (0.048 g, 0.21 mmol) and CH2Cl2 (2 ml) was added boron tribromide (1.05 ml of 1M sol. in CH2Cl2, 1.05 mmol), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was evaporated, methanol (2 ml) was added, the resulting mixture stirred for 1 hour and then evaporated. The resulting solid was purified by flash chromatography on SiO2 gel to yield the title compound (0.042 g, a 90% yield) as a solid. m.p.>250° C.; 1H NMR (400 MHz, DMSO) δ 7.28 (d, 1H, Ar), 7.47 (t, 1H, Ar), 7.75 (d, 1H, Ar), 9.06 (s, 1H, 2-CH), 10.36 (s, 1H, OH), 12.41 (s, 1H, NH).

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. additionmethanol (2 ml) was added
  3. stirringthe resulting mixture stirred for 1 hour
  4. customevaporated
  5. customThe resulting solid was purified by flash chromatography on SiO2 gel

Quellen und Nachweise

ORD-Eintrag
ord-0acb305522e042f48f24d512ddd4006d
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906935B2

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