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

HRID 11061

Reaction equation

HRID 11061 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3f6e1d2b349c474fa6a16a0f93f62613
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

Loading…