Triethylamine → 4-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide

HRID 7066

Reaktionsgleichung

Reaktionsgleichung von HRID 7066
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)#[CH:22].C(N(CC)CC)C>[Cu]I.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.C(#N)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:22]#[C:21][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 120966604-hydroxy-N-(3-iodophenyl)-3-methoxyphenylacetamide

Produkt 1

HCID 220196124-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamideAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178419050HCID 178419050, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of Intermediate 1 (2.5 g), ethynylbenzene (800 mg), copper (I) iodide (124 mg), bis(triphenylphosphine)palladium (II) dichloride (1.37 g), triethylamine (19.0 g) and acetonitrile (20 ml) is heated with stirring at 50° C. under argon atmosphere. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (1.8 g).

Aufarbeitung

  1. temperatureis heated
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-144fec4e7c764ed7b72601061fc955a2
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084176B2

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