Cesium carbonate → tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

HRID 2365387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365387
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:7]=3[N:8]2[CH3:11])=[CH:4][CH:3]=1.[CH2:23]([N:31]1[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(Cl)Cl.CO.[NH4+].[OH-].[Cu]I>[CH3:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([N:34]3[CH2:35][CH2:36][N:31]([CH2:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:32][C:33]3=[O:37])[CH:10]=2)[C:6]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C:7]1=2

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 85471654-Phenethylpiperazin-2-oneHCID 57950468tert-butyl 7-bromo-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate

Produkt 1

HCID 67986813tert-Butyl 9-methyl-7-(2-oxo-4-phenethylpiperazin-1-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylateAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 21896990Dichloromethane methanol ammonium hydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

tert-Butyl 7-bromo-9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (270 mg, 0.740 mmol), 4-phenethylpiperazin-2-one (150 mg, 0.735 mmol), CuI (140 mg, 0.735 mmol), trans-N,N′dimethylcyclohexane-1,2-diamine (104 mg, 0.735 mmol) and Cs2CO3 (311 mg, 0.956 mmol) in toluene (15 mL) were sparged with a nitrogen stream for 45 min and then stirred at 110° C. for 16 h. The mixture was diluted with 90:9:1 CH2Cl2/MeOH/NH4OH (50 mL) and washed with brine (3×50 mL). The resulting solution was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography eluting with methylene chloride and a 9:1 methanol/ammonium hydroxide mixture; gradient 100% methylene chloride to 85% methylene chloride, to provide the title compound (35 mg, 10%) as a yellow oil: ESI MS m/z 489 [M+H]+.

Aufarbeitung

  1. washwashed with brine (3×50 mL)
  2. dry with materialThe resulting solution was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography
  5. washeluting with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-885fcb4022344bffb16ee49e467d48b7
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697700B2

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