Tetrahydrofuran → 5-Bromo-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-amine

HRID 535381

Reaktionsgleichung

Reaktionsgleichung von HRID 535381
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1Br.[C:10]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])#[CH:11].C(N(CC)CC)C.C1COCC1>C(#N)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:9])=[N:6][C:7]=1[C:11]#[C:10][Si:12]([CH:13]([CH3:15])[CH3:14])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17]

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2734682(Triisopropylsilyl)acetyleneHCID 136927815,6-Dibromopyridin-2-amine

Produkt 1

HCID 866943665-Bromo-6-[2-tri(propan-2-yl)silylethynyl]pyridin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 5,6-dibromopyridin-2-amine (60 g, 233 mmol), ethynyl-tri(propan-2-yl)silane (64 ml, 285 mmol), copper(I) iodide (1.5 g, 7.88 mmol), Dichlorobis(triphenylphosphine)-palladium(II) (4.0 g, 5.48 mmol) and triethylamine (80 ml, 577 mmol) is stirred under argon atmosphere in ACN (200 ml) with THF (100 ml) for 2 h at 50° C. The mixture is concentrated in vacuo and the product purified by NP chromatography. Yield: 76 g (92%). HPLC-MS: M+H=353/355; tR=1.79 min (*Method—1).

Aufarbeitung

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by NP chromatography

Quellen und Nachweise

ORD-Eintrag
ord-03725f62953a43cb9ebe0a17b9fc9316
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859541B2

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