1-Benzylpiperazine → 1-triisopropylsilanyl-4-(4-benzyl-piperazin-1-yl)-1H-indole

HRID 1006415

Reaktionsgleichung

Reaktionsgleichung von HRID 1006415
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13].[CH2:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:15]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:12]([CH3:13])[CH3:14])[N:6]1[C:7]2[C:3](=[C:2]([N:31]3[CH2:32][CH2:33][N:28]([CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[CH2:29][CH2:30]3)[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1)([CH3:17])[CH3:16]

Komponenten

7

Edukt 4

HCID 759941-BenzylpiperazineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27955734-bromo-1-(triisopropylsilyl)-1H-indoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 226712611-triisopropylsilanyl-4-(4-benzyl-piperazin-1-yl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A mixture of 1.0 g (2.8 mmole) 4-bromo-triisopropylsilanyl-1H-indole, 0.54 mL (3.1 mmole) N-benzylpiperazine, 31 mg (0.14 mmole) palladium(II)acetate, 28 mg (0.14 mmole) tri-t-butylphosphine and 403 mg sodium t-butoxide in 5 mL xylene was heated at 120° for 15 hours. The reaction mixture was diluted with 100 mL 50% ether-hexane and filtered through a pad of silica gel 230-400 mesh. The filtrate was concentrated under reduced pressure to afford 1-triisopropylsilanyl-4-(4-benzyl-piperazin-1-yl)-1H-indole as a semi-solid, 1.2 g, M+H=448.

Aufarbeitung

  1. temperaturewas heated at 120° for 15 hours
  2. filtrationfiltered through a pad of silica gel 230-400 mesh
  3. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d5112bf2dea042d1bf1a27dcc81af0ac
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790848B2

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