Trimethylsilylacetylene → 3-Nitro-5-((trimethylsilyl)ethynyl)pyridine

HRID 2271653

Reaktionsgleichung

Reaktionsgleichung von HRID 2271653
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:11]([Si:13]([CH3:16])([CH3:15])[CH3:14])#[CH:12]>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)I>[N+:8]([C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:12]#[C:11][Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1)([O-:10])=[O:9]

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 27628983-Bromo-5-nitropyridine

Produkt 1

HCID 667157023-Nitro-5-((trimethylsilyl)ethynyl)pyridineAusbeute 159,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 3-bromo-5-nitropyridine (1.0 g, 4.90 mmol), Pd(Ph3P)4 (0.57 g, 0.49 mmol), and copper iodide (0.19 g, 0.98 mmol) in triethylamine (30 mL) was added ethynyltrimethylsilane (1.0 mL, 7.35 mmol) and the reaction was purged with N2. The mixture was stirred at 80° C. for 2 h. The reaction mixture was filtered through celite and washed with ethyl acetate. The filtrate was washed with saturated solutions of NaHCO3 and NaCl. The organic layer was concentrated to afford the crude product (1.72 g) as a light brown solid: ESI MS m/z 221 [C10H12N2O2Si+H]+.

Aufarbeitung

  1. customthe reaction was purged with N2
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with ethyl acetate
  4. washThe filtrate was washed with saturated solutions of NaHCO3 and NaCl
  5. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ca7f18693e3641b992c4d5a3cef535c2
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120749B2

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