Triethylamine → 5-Methyl-2-(2-(trimethylsilyl)ethynyl)pyridine

HRID 2175418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175418
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[C:9]([Si:11]([CH3:14])([CH3:13])[CH3:12])#[CH:10].C(N(CC)CC)C>[Cu](I)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>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]#[C:9][Si:11]([CH3:14])([CH3:13])[CH3:12])=[N:3][CH:4]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 5642162-Bromo-5-methylpyridine

Produkt 1

HCID 447549315-Methyl-2-(2-(trimethylsilyl)ethynyl)pyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

The mixture of 2-bromo-5-methylpyridine (5.0 g, 29.1 mmol), ethynyltrimethylsilane (3.42 g, 34.88 mmol), Copper iodide (0.61 g, 332 mg) and Pd(PPh3)2Cl2 (0.61 g, 0.871 mmol) was dissolved in triethylamine (6.4 mL, 261 mmol). The solution was purged with N2 3 times. The solution was stirred for overnight under 25° C. The solvent was removed under reduced pressure. The residue was separated by silca gel chromatography with the eluent of PE/EA=20/1. The product was obtained as a yellow solid (4.15 g, 76%). 1H NMR (400 MHz, CDCl3) δ 8.41 (s, 1H), 7.46 (dd, J=7.9, 1.5 Hz, 1H), 7.36 (d, J=7.9 Hz, 1H), 2.35 (s, 3H), 0.28 (s, 9H); LRMS (ES) calculated M+H for C11H16NSi: 190.3. Found: 190.2.

Aufarbeitung

  1. customThe solution was purged with N2 3 times
  2. customThe solvent was removed under reduced pressure
  3. customThe residue was separated by silca gel chromatography with the eluent of PE/EA=20/1

Quellen und Nachweise

ORD-Eintrag
ord-51860b5220224f50878726ba5d29a3f0
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062059B2

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