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

HRID 11060ノート

反応式

HRID 11060 の反応式
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

参加物

8

反応物 5

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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8ee1968d724d49868e7cadce4af9eada
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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