Triethylamine → 3-Fluoro-5-phenylethynylpyridine

HRID 606844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606844
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:16][C:17]1[CH:18]=[C:19](OS(C(F)(F)F)(=O)=O)[CH:20]=[N:21][CH:22]=1>C(OCC)(=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:16][C:17]1[CH:22]=[N:21][CH:20]=[C:19]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:18]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11413882Methanesulfonic acid, trifluoro-, 5-fluoro-3-pyridinyl ester

Produkt 1

HCID 670474963-Fluoro-5-phenylethynylpyridineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178419050HCID 178419050, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Add phenylacetylene (0.180 mL, 1.6 mmol), copper (I) iodide (0.015 g, 0.08 mmol) bis(triphenylphosphine)palladium (II) dichloride (0.027 g. 0.04 mmol) and triethylamine (0.85 mL, 6 mmol) to a solution of trifluoromethanesulfonic acid 5-fluoro-pyridin-3-yl ester, (prepared essentially as described in PREPARATION 6), (0.367 g, 1.5 mmol) in degassed ethyl acetate (1.5 mL) and heat at 60° C. for 16 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, wash with ethyl acetate, and concentrate. Purify the residue by silica gel chromatography, eluting with dichloromethane, to give the title compound (0.192 g, 65%).

Aufarbeitung

  1. custom(prepared essentially
  2. temperatureCool the reaction mixture to room temperature
  3. filtrationfilter through diatomaceous earth
  4. washwash with ethyl acetate
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-55c22a639733475fa7dc8b4eaaabb4ef
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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