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Water → 13-(2-Cyanoethyl)-6,7,12,13-tetrahydro-3-hydroxy-12-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole

HRID 1418631
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HRID 1418631 반응식
[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:14]3[N:15]([CH3:29])[C:16]4[C:21]([C:22]=3[C:23]3[CH2:27][NH:26][C:25](=[O:28])[C:24]=3[C:12]=2[C:11]2[CH:10]=[C:9]([O:30]C)[CH2:8][C:7](=O)[C:6]1=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)#[N:2].B(Br)(Br)Br.O.C([O:41]C(C)C)(C)C.CC(C)=O>ClCCl.O1CCCC1>[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:14]3[N:15]([CH3:29])[C:16]4[C:21]([C:22]=3[C:23]3[C:27](=[O:41])[NH:26][C:25](=[O:28])[C:24]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]1=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)#[N:2]
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7

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HCID 962WaterHCID 25134Boron tribromide2회HCID 22221350Acetone diisopropyl etherHCID 8675390513-(2-cyanoethyl)-6,7,12,13-tetrahydro-3-methoxy-12-methyl-5,1-dioxo-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole

생성물 1

HCID 2121685613-(2-Cyanoethyl)-6,7,12,13-tetrahydro-3-hydroxy-12-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole

시약·촉매·용매

2
HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

200 mg (0.45 mmol) 13-(2-cyanoethyl)-6,7,12,13-tetrahydro-3-methoxy-12-methyl-5,1-dioxo-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole (Example 1) in 15 ml dichloromethane are cooled to -10° C. and 0.1 ml (0.7 mmol) of a 1M solution of boron tribromide in dichloromethane added dropwise thereto. Since, after 3 hours at -10° C., no reaction is shown (TLC), 1.4 ml of the 1M solution of boron tribromide are again added thereto, followed by stirring for 16 hours at 20° C. 100 ml of water and 100 ml tetrahydrofuran are added thereto and the organic phase is separated off, washed with 100 ml of water and dried over anhydrous sodium sulphate. After filtration and evaporation, the residue is first chromatographed with dichloro-methane/methanol (95:5 v/v) and then again with toluene/tetrahydrofuran (4:1 v/v). The fraction with the Rf 0.3 in toluene/tetrahydrofuran (2:1 v/v) is isolated, stirred with diisopropyl ether/acetone and the crystals formed are filtered off. 13-(2-Cyanoethyl)-6,7,12,13-tetrahydro-3-hydroxy-12-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of yellow crystals which decompose from about 315° C.

후처리

  1. additionare again added
  2. customthe organic phase is separated off
  3. washwashed with 100 ml of water
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationAfter filtration and evaporation
  6. customthe residue is first chromatographed with dichloro-methane/methanol (95:5 v/v)
  7. customThe fraction with the Rf 0.3 in toluene/tetrahydrofuran (2:1 v/v) is isolated
  8. customthe crystals formed
  9. filtrationare filtered off

출처 및 근거

ORD 기록
ord-11e8040c73dc47efa63a29585f7f0297
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05883114

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