Ethyl 3-(trimethylsilyl)propynoate → 1-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

HRID 1454976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454976
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.[CH3:17][Si:18]([CH3:27])([CH3:26])[C:19]#[C:20][C:21](OCC)=[O:22]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:9]2[C:10]([F:16])=[CH:11][CH:12]=[CH:13][C:14]=2[F:15])[C:21](=[O:22])[C:20]#[C:19][Si:18]([CH3:27])([CH3:26])[CH3:17])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 568601Ethyl 3-(trimethylsilyl)propynoateHCID 575312355-Bromo-2-(2,6-difluorobenzyl)pyridine

Produkt 1

HCID 575312421-(5-Bromopyridin-2-yl)-1-(2,6-difluorophenyl)-4-(trimethylsilyl)but-3-yn-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 5-bromo-2-(2,6-difluorobenzyl)pyridine (5.6 g) in THF was added ethyl 3-(trimethylsily)propynoate (4.2 mL) and LHMD (42 mL, 1N in THF) at −78° C. The mixture was warmed to 0° C. and stirred in additional 2 h. The reaction was complete by TLC and quenched with NH4Cl, extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4 and condensed in vacuo. The crude compound was purified by silica gel (hexanes/methylene chloride) to give the desired product.

Aufarbeitung

  1. customquenched with NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4 and condensed in vacuo
  5. customThe crude compound was purified by silica gel (hexanes/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-bae2a9105a944a8293550526683bebbf
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482345B2

Notizen zur Reaktion

Wird geladen…