반응 #11158

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5-Methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole

2-[(E)-2-(2-Bromo-4-nitrophenyl)ethenyl]-5-methoxy-1H-indole

3-bromopropyl tert-butyl(dimethyl)silyl ether

maleimide

→

alcohol

수율 23.0%

6-(3-Hydroxypropyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

수율 23.0%

용매

water

methanol

hydrochloric acid

반응 조건

후처리

1. 1
   기타The product isolated
2. 2
   기타gave crude material that
3. 3
   workup.ADDITIONwas added
4. 4
   추출extracted with ethyl acetate
5. 5
   기타The organic layer was dried
6. 6
   기타the drying agent was removed
7. 7
   농축the solution was concentrated to dryness
8. 8
   기타chromatographed
9. 9
   세척eluting with dichloromethane to ethyl acetate/dichloromethane (7:3)

실험 절차

5-Methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole (II; Ar=phenyl) (6.85 g, 27.5 mmol) was reacted with with 3-bromopropyl tert-butyl(dimethyl)silyl ether using the procedure described in example 38. The product isolated was reacted directly with maleimide (5.2 g) using the procedure described in example 68. Aromatisation of the crude Diels-Alder adduct using the procedure described in example 79 gave crude material that was then dissolved in methanol (300 mL) to which 1N hydrochloric acid (50 mL) was added. This solution was stirred at rt for 3h before being diluted with water and extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. The residue was adsorbed onto silica and chromatographed eluting with dichloromethane to ethyl acetate/dichloromethane (7:3). Trituration with diethyl ether gave alcohol (202) as a yellow powder (2.55 g, 23%), mp 241–243° C. 1H NMR δ [(CD3)2SO] 11.10 (br s, 1H), 8.56 (d, J=2.6 Hz, 1H), 7.82 (s, 1H), 7.67 (m, 3H), 7.47 (m, 3H), 7.30 (dd. J=9.0, 2.6 Hz, 1H), 4.66 (t, J=4.9 Hz, 1H), 4.55 (t, J=6.9 Hz, 2H), 3.90 (s, 3H), 3.39 (m. 2H), 1.93 (m, 2H). Found: C, 71.95; H, 5.09; N, 6.93. C24H20N2O4 requires: C, 71.99; H. 5.03; N. 6.99.

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