Water → 4-(2-chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11060Notes

Reaction equation

HRID 11060 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:24]2[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:23]=2[C:22]2[C:21]3[CH:20]=[C:19]([O:30]C)[CH:18]=[CH:17][C:16]=3[N:15]([CH2:32][CH2:33][CH2:34][OH:35])[C:14]=2[CH:13]=1.CO[C:38]1[CH:39]=[C:40]2[C:44](=[CH:45][CH:46]=1)[NH:43][C:42]([CH:47]=[CH:48][C:49]1[CH:54]=[C:53]([N+:55]([O-:57])=[O:56])[CH:52]=[C:51]([N+]([O-])=O)[CH:50]=1)=[CH:41]2.[C:61]([O-])(O)=[O:62].[Na+].[OH2:66]>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[C:24]2[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:23]=2[C:22]2[C:21]3[CH:20]=[C:19]([OH:30])[CH:18]=[CH:17][C:16]=3[N:15]([CH2:32][CH2:33][CH2:34][OH:35])[C:14]=2[CH:13]=1.[OH:66][C:38]1[CH:46]=[CH:45][C:44]2[NH:43][C:42]3[CH:47]=[C:48]([C:49]4[CH:54]=[C:53]([N+:55]([O-:57])=[O:56])[CH:52]=[CH:51][C:50]=4[O:62][CH3:61])[C:24]4[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:23]=4[C:41]=3[C:40]=2[CH:39]=1

Participants

8

Reactant 5

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21980629HCID 21980629, compoundHCID 867601905-Methoxy-2-[2-(3,5-dinitrophenyl)ethenyl]-1H-indole

Product 2

HCID 248846964-(2-chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 697128459-hydroxy-4-(2-methoxy-5-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1N BBr3 in CH2Cl2 (11.5 mL, 0.011 mol) was added to a solution of 4-(2-Chlorophenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chlorophenyl, R10═CH2CH2CH2OH) (31) prepared as described in example 40 (1.00 g, 2.30 mmol) in CH2Cl2 under nitrogen and the reaction mixture was stirred at room temperature for 3 h. Saturated aqueous NaHCO3 solution was added and the solution was 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, adsorbed onto silica and chromatographed. Elution with ethyl acetate/petroleum ether (1:1) followed by ethyl acetate gave 4-(2-Chlorophenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chlorophenyl, R10═CH2CH2CH2OH) (34) in a yield of 0.90 g, 93%, which crystallised from THF/petroleum ether as a yellow/orange powder, mp 291–294° C. 1H NMR δ [(CD3)2SO 11.05 (br s, 1H), 9.36 (s, 1H), 8.38 (d, J=2.5 Hz, 1H), 7.74 (s, 1H), 7.59–7.54 (m, 2H), 7.52–7.42 (m, 3H), 7.14 (dd, J=8.7, 2.5 Hz, 1H), 4.62 (br t, 1H), 4.49 (t, J=6.8 Hz, 2H), 3.41 (m, 2H), 1.90 (m, 2H). Found: C, 64.99; H, 4.13; N, 6.43. C23H17ClN2O4.1/4H2O requires C, 64.94; H, 4.15; N, 6.58.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was dried
  3. customthe drying agent was removed
  4. concentrationthe solution was concentrated to dryness
  5. customchromatographed
  6. washElution with ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-8ee1968d724d49868e7cadce4af9eada
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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