N-Triisopropylsilylpyrrole → 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole

HRID 2220438

Reaktionsgleichung

Reaktionsgleichung von HRID 2220438
[CH:1]([Si:4]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[N:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1)([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[C:19]([C:23]#[CH:24])[CH:20]=[CH:21][CH:22]=1>CC#N.C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Br:16][C:17]1[CH:18]=[C:19]([C:23]#[C:24][C:7]2[CH:8]=[CH:9][N:5]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:10]([CH3:12])[CH3:11])[CH:13]([CH3:15])[CH3:14])[CH:6]=2)[CH:20]=[CH:21][CH:22]=1

Komponenten

7

Edukt 2

HCID 145136N-TriisopropylsilylpyrroleHCID 114808181-Bromo-3-ethynylbenzene

Produkt 1

HCID 687008993-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrroleAusbeute 670,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of N-triisopropylsilylpyrrole (3.49 g, 1 mmol), 3-bromo-1-ethynylbenzene (1.81 g, 1 mmol), Pd(PPh3)4 (800 mg) and CuI (185 mg) in CH3CN (15 ml) and triethylamine (35 ml) is refluxed for 5 h. The reaction mixture is cooled to room temperature and the solvent is evaporated on a rotary evaporator. The crude material is purified by flash chromatographied (silica gel, 100% hexane) to afford 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole (2.7 g, 85%) as a clear oil.

Aufarbeitung

  1. customthe solvent is evaporated on a rotary evaporator
  2. customThe crude material is purified by flash

Quellen und Nachweise

ORD-Eintrag
ord-8624bbc06062466d8de67d6cbe536bc0
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417047B2

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