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

HRID 11062

반응식

HRID 11062 반응식
Br[C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][C:3]=1/[CH:11]=[CH:12]/[C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([O:22][CH3:23])=[CH:17][CH:16]=2.[Si]([O:31][CH2:32][CH2:33][CH2:34]Br)(C(C)(C)C)(C)C.[C:36]1(=[O:42])[NH:40][C:39](=[O:41])[CH:38]=[CH:37]1>CO.Cl.O>[OH:31][CH2:32][CH2:33][CH2:34][N:14]1[C:13]2[CH:12]=[C:11]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=3)[C:37]3[C:36](=[O:42])[NH:40][C:39](=[O:41])[C:38]=3[C:21]=2[C:20]2[CH:19]=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][C:15]1=2

참가 물질

7

반응물 3

HCID 10935MaleimideHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 219808902-[(e)-2-(2-Bromo-4-nitrophenyl)ethenyl]-5-methoxy-1h-indole

생성물 1

HCID 867601996-(3-Hydroxypropyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione수율 23%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887Methanol용매HCID 962Water용매

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.

후처리

  1. customThe product isolated
  2. customgave crude material that
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. customthe drying agent was removed
  7. concentrationthe solution was concentrated to dryness
  8. customchromatographed
  9. washeluting with dichloromethane to ethyl acetate/dichloromethane (7:3)

출처 및 근거

ORD 기록
ord-f61fe06652e1483ba61e938ea5e32000
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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