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

HRID 11060노트

반응식

HRID 11060 반응식
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

참가 물질

8

반응물 5

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

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8ee1968d724d49868e7cadce4af9eada
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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