Trimethylsilyl iodide → 4-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide

HRID 2361406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2361406
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[C:14]([C:15]4[C:16]([CH3:32])=[C:17]([NH:21]C(=O)OCC5C=CC=CC=5)[CH:18]=[CH:19][CH:20]=4)=[C:13]([CH3:33])[N:12]=[C:11]([C:34](=[O:36])[NH2:35])[C:7]=3[NH:8]2)=[CH:4][CH:3]=1.I[Si](C)(C)C>C(#N)C>[NH2:21][C:17]1[C:16]([CH3:32])=[C:15]([C:14]2[C:6]3[C:5]4[C:9](=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=4)[NH:8][C:7]=3[C:11]([C:34]([NH2:35])=[O:36])=[N:12][C:13]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 85247Trimethylsilyl iodideHCID 70651685benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate

Produkt 1

HCID 679952474-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of benzyl (3-(7-bromo-1-carbamoyl-3-methyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenyl)carbamate (1.10 g, 2.02 mmol) in acetonitrile (100 mL) at 0° C. was added iodotrimethylsilane (1.10 mL, 8.10 mmol) dropwise. The mixture was stirred at room temperature for 1.5 h. After concentration, diethylamine (2 mL) and ethyl acetate (150 mL) were added to the residue. The mixture was washed with water (2×40 mL), washed with brine (40 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by purification by flash silica gel chromatography using a mixture of ethyl acetate in hexane (20%-35%-50%) afforded 4-(3-amino-2-methylphenyl)-7-bromo-3-methyl-9H-pyrido[3,4-b]indole-1-carboxamide (0.411 g, 1.00 mmol, 50% yield) as a tan solid. LC/MS M+1=409.1 and 411.1.

Aufarbeitung

  1. concentrationAfter concentration, diethylamine (2 mL) and ethyl acetate (150 mL)
  2. additionwere added to the residue
  3. washThe mixture was washed with water (2×40 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under reduced pressure
  7. customfollowed by purification by flash silica gel chromatography
  8. additiona mixture of ethyl acetate in hexane (20%-35%-50%)

Quellen und Nachweise

ORD-Eintrag
ord-92d8aa786db04b7a9e7f2cc69ba61c67
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685969B2

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