p-Toluenesulfonic acid → 6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11061

反応式

HRID 11061 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.Br[CH2:25][CH2:26][O:27]C1CCCCO1.[C:34]1(=[O:40])[NH:38][C:37](=[O:39])[CH:36]=[CH:35]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O>[OH:27][CH2:26][CH2:25][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:35]3[C:34](=[O:40])[NH:38][C:37](=[O:39])[C:36]=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 4

HCID 6101p-Toluenesulfonic acidHCID 10935MaleimideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 219808902-[(e)-2-(2-Bromo-4-nitrophenyl)ethenyl]-5-methoxy-1h-indole

生成物 1

HCID 867601986-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

5-methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole (II; Ar=phenyl) (1.93 g, 7.74 mmol was reacted with 2-(2-bromoethoxy)tetrahydro-2H-pyran using the procedure described in example 38. This material was reacted directly with maleimide (0.79 g) using the procedure described in method 4. The product obtained was reacted using the procedure described in example 70 gave crude material that was then dissolved in methanol (100 mL) to which p-toluenesulfonic acid (30 mg) was added before the solution was warmed to 50° C. for 3h. The solution was then diluted with water and extracted with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness before being adsorbed onto silica and chromatographed eluting with ethyl acetate/hexane (1:2 to 1:1) to give 6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=phenyl, R10═(CH2)2OH) (201) in a yield of 0.51 g, 17% as a yellow powder; mp 262–264° C. 1H NMR δ [(CD3)2SO] 11.09 (br s, 1H), 8.56 (d, J=2.6 Hz, 1H), 7.83 (s, 1H), 7.66 (m, 3H), 7.47 (m, 3H), 7.28 (dd, J=9.0, 2.6 Hz, 1H), 4.86 (t, J=5.5 Hz, 1H), 4.55 (t, J=5.3 Hz, 2H), 3.90 (s, 3H), 3.78 (m, 2H). Found: C, 71.47; H. 4.77; N, 7.32. C23H18N2O4 requires: C, 71.49; H, 4.70; N, 7.25.

後処理

  1. customThe product obtained
  2. customwas reacted
  3. customgave crude material that
  4. additionwas added before the solution
  5. extractionextracted with ethyl acetate
  6. customThe organic phase was dried
  7. customthe drying agent was removed
  8. concentrationthe solution was concentrated to dryness
  9. customchromatographed
  10. washeluting with ethyl acetate/hexane (1:2 to 1:1)

出典と根拠

ORDレコード
ord-3f6e1d2b349c474fa6a16a0f93f62613
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

関連ノート

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