Iodine → 5-(3-Cyano-4-fluorophenylethynyl)-nicotinonitrile

HRID 606952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606952
[OH-].[NH4+:2].II.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=2)[C:19]#[N:20])=[CH:8][C:7]=1[CH:22]=O>O1CCCC1>[C:22]([C:7]1[CH:8]=[C:9]([C:12]#[C:13][C:14]2[CH:15]=[N:16][CH:17]=[C:18]([CH:21]=2)[C:19]#[N:20])[CH:10]=[CH:11][C:6]=1[F:5])#[N:2]

Komponenten

5

Edukt 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 848197895-((4-Fluoro-3-formylphenyl)ethynyl)nicotinonitrile

Produkt 1

HCID 670476325-(3-Cyano-4-fluorophenylethynyl)-nicotinonitrileAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add a 28% aqueous solution of ammonium hydroxide (10 mL) and iodine (279 mg, 1.10 mmol) to a solution of 5-(4-fluoro-3-formylphenylethynyl) -nicotinonitrile, (prepared as described in PREPARATION 38), (250 mg, 1.00 mmol) in tetrahydrofuran (5 mL). After 3.25 h quench with a 5% aqueous solution of sodium bisulfite (5 mL) and extract twice with ethyl acetate. Wash the organic layers with saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate. Dissolve the crude solid in dichloromethane and add PS-TsNNH2 (3g, ˜1.2 mmol, Argonaut). Stir the mixture for 20 min and filter through diatomaceous earth. Purify by silica gel chromatography, eluting with 90:10 to 80:20 (70:30 hexanes:dichloromethane):ethyl acetate, to give the title compound as a white crystalline solid (140 mg, 57%).

Aufarbeitung

  1. customAfter 3.25 h quench with a 5% aqueous solution of sodium bisulfite (5 mL)
  2. extractionextract twice with ethyl acetate
  3. washWash the organic layers with saturated aqueous sodium chloride
  4. dry with materialdry (sodium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. dissolutionDissolve the crude solid in dichloromethane
  8. additionadd PS-TsNNH2 (3g, ˜1.2 mmol, Argonaut)
  9. filtrationfilter through diatomaceous earth
  10. customPurify by silica gel chromatography
  11. washeluting with 90:10 to 80:20 (70:30 hexanes:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-07202ce9c4004f88810bc05d6b528441
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915424B2

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