Tetrahydrofuran → 4-(2-Chlorophenyl)-6-methyl-9-(methylamino)pyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione

HRID 11166

Reaktionsgleichung

Reaktionsgleichung von HRID 11166
COB(OC)OC.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:27]2[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:26]=2[C:25]2[C:24]3[CH:23]=[C:22]([NH:33][CH:34]=O)[CH:21]=[CH:20][C:19]=3[N:18]([CH3:36])[C:17]=2[CH:16]=1.O1CCCC1>CO>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:27]2[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:26]=2[C:25]2[C:24]3[CH:23]=[C:22]([NH:33][CH3:34])[CH:21]=[CH:20][C:19]=3[N:18]([CH3:36])[C:17]=2[CH:16]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 8470Trimethyl borateHCID 878991884-(2-Chlorophenyl)-6-methyl-1,3-dioxo-1,2,3,6-tetrahydropyrrolo[3,4-c]carbazol-9-ylformamide

Produkt 1

HCID 219808324-(2-Chlorophenyl)-6-methyl-9-(methylamino)pyrrolo[3,4-c]carbazole-1,3(2h,6h)-dioneAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Borane methylsulphide complex (0.074 mL, 0.78 mmol) and trimethylborate (0.089 mL, 0.78 mmol) were added at 0° C. under an atmosphere of nitrogen to a solution of amide (920) (0.105 g, 0.26 mmol) prepared as described in example 469 dry tetrahydrofuran (10 mL) After stirring at 0° C. for 30 min. the solution was allowed to warm to room temperature over 16 h. Methanol (200 mL) was added and the reaction mixture was stirred for 12 h. The solvent was removed under reduced pressure and the yellow residue was purificatied by column chromatography on silica, eluting with petroleum ether:ethyl acetate (100:0 to 0:100) to give (922) as a red solid (0.053 g, 45%), mp 293–296° C. 1H NMR δ [(CD3)2SO] 11.01 (br s, 1H), 8.10 (d, J=2.3 Hz, 1H), 7.69 (s, 1H), 7.57 (dd, J=7.1, 2.0 Hz, 1H), 7.42–7.52 (m, 4H), 7.02 (dd, J=8.8, 2.3 Hz, 1H), 5.61 (q, J=5.2 Hz, 1H), 3.90 (s, 3H), 2.81 (d, J=5.2 Hz, 3H). EIMS found: M+=389.0929, 391.0905. C22H16ClN3O2 requires 389.0931, 391.0902.

Aufarbeitung

  1. customprepared
  2. temperatureto warm to room temperature over 16 h
  3. stirringthe reaction mixture was stirred for 12 h
  4. customThe solvent was removed under reduced pressure
  5. washeluting with petroleum ether:ethyl acetate (100:0 to 0:100)

Quellen und Nachweise

ORD-Eintrag
ord-5f54c01cc7bf4ef68d7dd7fbd24d551f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

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