Sodium hydride → 2-Fluoro-3-{3-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrol-2-yl}pyridine

HRID 869737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869737
[H-].[Na+].[F:3][C:4]1[C:9]([C:10]2[NH:11][CH:12]=[CH:13][C:14]=2[F:15])=[CH:8][CH:7]=[CH:6][N:5]=1.C1OCCOCCOCCOCCOC1.FC(F)(F)S(O[Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])(=O)=O>O1CCCC1>[F:3][C:4]1[C:9]([C:10]2[N:11]([Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[CH:12]=[CH:13][C:14]=2[F:15])=[CH:8][CH:7]=[CH:6][N:5]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 583498262-fluoro-3-(3-fluoro-1H-pyrrol-2-yl)pyridine

Produkt 1

HCID 671787532-Fluoro-3-{3-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrol-2-yl}pyridineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (3.32 g) in tetrahydrofuran (70 mL) was added dropwise a solution of 2-fluoro-3-(3-fluoro-1H-pyrrol-2-yl)pyridine (5.98 g) in tetrahydrofuran (30 mL) under ice-cooling and the mixture was stirred for 30 min. 15-Crown-5 (18.3 g) and tris(1-methylethyl)silyl trifluoromethanesulfonate (25.4 g) were added, and the mixture was stirred for 1 hr. The solvent was evaporated to a half volume under reduced pressure, water was added, and the mixture was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:hexane hexane-ethyl acetate=19:1) to give the title compound as a pale-yellow oil (yield 10.9 g, 98%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. customThe solvent was evaporated to a half volume under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe separated aqueous layer was extracted again with ethyl acetate
  7. washCombined organic layers were washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by basic silica gel column chromatography (eluent:hexane hexane-ethyl acetate=19:1)

Quellen und Nachweise

ORD-Eintrag
ord-34c081d372ec46978005235a6459aff5
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969387B2

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