Reaktion #11228

Reaktionsgleichung

triflate

4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-8-yl trifluoromethanesulfonate

(3E)-4-(tributylstannyl)-3-buten-1-ol

ethyl acetate

lithium chloride

→

( 170 )

Ausbeute 95.9%

4-(2-Chlorophenyl)-8-[(1E)-4-hydroxy-1-butenyl]-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Ausbeute 95.9%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged
2. 2
   Sonstigeby bubbling nitrogen through the liquid for 10 min
3. 3
   Sonstigethe solution was flushed with nitrogen for 2 min more
4. 4
   Temperaturwarmed under an atmosphere of nitrogen for 3 h
5. 5
   workup.ADDITIONThe mixture was diluted with brine
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   Sonstigeto give an oil which
8. 8
   Sonstigewas chromatographed on silica
9. 9
   WaschenElution with ethyl acetate/petroleum ether (1:5)
10. 10
    Sonstigegave foreruns

Vorschrift

A solution of the triflate (169) (0.20 g, 0.35 mmol) prepared as described in example 308, (3E)-4-(tributylstannyl)-3-buten-1-ol (0.19 g, 0.53 mmol) and lithium chloride (29 mg, 0.70 mmol) in DMF (10 mL) was purged by bubbling nitrogen through the liquid for 10 min. Bis(triphenylphosphine)palladium dichloride (12 mg, 0.017 mmol) was added last and the solution was flushed with nitrogen for 2 min more, then warmed under an atmosphere of nitrogen for 3 h. The mixture was diluted with brine, extracted with ethyl acetate and worked up to give an oil which was chromatographed on silica. Elution with ethyl acetate/petroleum ether (1:5) gave foreruns, while ethyl acetate/petroleum ether (1:1) increasing to pure ethyl acetate gave (170) as a yellow solid (0.15 g, 95%), mp 271–275° C. 1H NMR δ [(CD3)2SO] 11.86 (br s, 1H), 11.07 (br s, 1H), 8.45 (s, 1H), 7.70 (s, 1H), 7.58 (dd, J=8.1, 2.2 Hz, 1H), 7.55 (s, 1H), 7.51–7.41 (m, 3H), 6.87 (d, J=16.0 Hz, 1H), 6.44 (dt, J=16.0, 7.1 Hz, 1H), 4.62 (t, J=5.3 Hz, 1H), 3.94 (s, 3H), 3.58 (m, 2H), 2.42 (m, 2H). Found: C, 67.09; H, 4.36; N, 5.98. C25H19ClN2O4 requires C, 67.19; H, 4.28; N, 6.27.

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