Tetrahydrofuran → 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

HRID 606799

Reaktionsgleichung

Reaktionsgleichung von HRID 606799
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.I[C:25]1[CH:26]=[C:27]([F:31])[CH:28]=[CH:29][CH:30]=1.[CH2:32]([O:34][C:35](=[O:48])[C:36]1[CH:41]=[C:40]([C:42]#[C:43][Si](C)(C)C)[CH:39]=[N:38][CH:37]=1)[CH3:33].[Cl-].[NH4+]>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.[Cu]I>[CH2:32]([O:34][C:35](=[O:48])[C:36]1[CH:41]=[C:40]([C:42]#[C:43][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)[CH:39]=[N:38][CH:37]=1)[CH3:33]

Komponenten

9

Edukt 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 707251-Fluoro-3-iodobenzeneHCID 2724141Tetrabutylammonium FluorideHCID 67047749Ethyl 5-((trimethylsilyl)ethynyl)nicotinate

Produkt 1

HCID 670477625-(3-Fluorophenylethynyl)-nicotinic acid ethyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178419050HCID 178419050, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Add a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.88 g, 3.38 mmol) to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester (0.84 g, 3.38 mmol), (prepared essentially as described in PREPARATION 16), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −780C. Warm to room temperature, stir overnight and dilute the mixture with ethyl acetate and an aqueous saturated solution of ammonium chloride. Separate the organic layer; dry (magnesium sulfate), filter and concentrate. Purify the resulting residue by silica gel chromatography, eluting with 2.5:45:52.5 ethyl acetate:chloroform:hexanes, to give the title compound as a pale yellow solid (0.46 g, 80%).

Aufarbeitung

  1. custom(prepared essentially
  2. customSeparate the organic layer
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the resulting residue by silica gel chromatography
  7. washeluting with 2.5:45:52.5 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a0fe3f254a904a1c9d2c2616b051a16f
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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