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 1586592Notes

Reaction equation

HRID 1586592 reaction equation
[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]

Participants

7

Reactant 4

HCID 962WaterHCID 25134Boron tribromide2×HCID 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

Product 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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

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 dichloromethane/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.

Workup

  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 dichloromethane/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

Sources & evidence

ORD record
ord-87a90c96c98947c18641e2b66669a5c9
Source dataset
uspto-grants-1999_08
Patent number
US05945440

Reaction notes

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