Propargyl alcohol → N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamide

HRID 1247579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247579
[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16](Br)[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([OH:26])[C:24]#[CH:25]>[Cu]I.C(NCC)C>[C:1]12([CH2:11][NH:12][C:13](=[O:22])[C:14]3[C:19]([Cl:20])=[CH:18][N:17]=[C:16]([C:25]#[C:24][CH2:23][OH:26])[CH:15]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

5

Edukt 2

HCID 7859Propargyl alcoholHCID 11773529N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide

Produkt 1

HCID 21906723N-(1-Adamantylmethyl)-5-chloro-2-(3-hydroxy-1-propynyl)isonicotinamideAusbeute 53,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A mixture of N-(1-adamantylmethyl)-2-bromo-5-chloroisonicotinamide (Example 1(ii)) (0.96 g), propargyl alcohol (0.16 g), copper (I) iodide, bis-triphenylphosphine palladium is dichloride (0.035 g) and diethylamine (10 ml) was stirred together at room temperature for 20 hours. The mixture was concentrated and the residue partitioned between ethyl acetate and 1M aqueous hydrochloric acid solution (2×25 ml) and the mixture was extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica gel eluting with ethyl acetate:iso-hexane (1:4 to 1:1) and then ethyl acetate to afford the sub-titled compound (0.48 g) as an oil.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and 1M aqueous hydrochloric acid solution (2×25 ml)
  3. extractionthe mixture was extracted into ethyl acetate (3×25 ml)
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel eluting with ethyl acetate:iso-hexane (1:4 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ca47c98aa6d046849e2f7a0a43917eeb
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129246B2

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