反応 #11158

反応方程式

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

収率 23.0%

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

収率 23.0%

溶媒

water

methanol

hydrochloric acid

反応条件

後処理

1. 1
   その他The product isolated
2. 2
   その他gave crude material that
3. 3
   workup.ADDITIONwas added
4. 4
   抽出extracted with ethyl acetate
5. 5
   その他The organic layer was dried
6. 6
   その他the drying agent was removed
7. 7
   濃縮the solution was concentrated to dryness
8. 8
   その他chromatographed
9. 9
   洗浄eluting with dichloromethane to ethyl acetate/dichloromethane (7:3)

実験手順

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.

出典