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

HRID 11062

反応式

HRID 11062 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f61fe06652e1483ba61e938ea5e32000
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

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