Triethylamine → 5-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 402595

Reaktionsgleichung

Reaktionsgleichung von HRID 402595
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18]>O1CCCC1.C(OCC)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>[NH2:1][C:2]1[C:7]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

Produkt 1

HCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amineAusbeute 109,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, to a solution of 2-amino-5-chloro-3-iodopyridine (4.2 g, 0.017 mol), copper(I) iodide (0.032 g, 0.17 mmol) and triethylamine (7.0 mL, 0.050 mol) in anhydrous tetrahydrofuran (10 mL), dichlorobis(triphenylphosphine)palladium(II) (0.12 g, 0.17 mmol) and ethynyl trimethylsilane (3.0 mL, 0.021 mol) were added and the mixture was stirred at ambient temperature for 2 h. The reaction mixture was diluted with diethyl ether and removed the precipitate by filtration with C elite. The filtrate was concentrated to afford 2-amino-5-chloro-3-[(trimethylsilyl)ethynyl]pyridine as solid (4.2 g).

Aufarbeitung

  1. customremoved the precipitate
  2. filtrationby filtration with C elite
  3. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-84fa41631148433bab00c109d60ee98d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742113B2

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