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

HRID 11061

반응식

HRID 11061 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.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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3f6e1d2b349c474fa6a16a0f93f62613
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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