Triethylamine → (4-Bromo-2-phenylethynyl-thiazol-5-yl)-piperidin-1-yl-methanone

HRID 2092969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2092969
Br[C:2]1[S:3][C:4]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[C:5]([Br:7])[N:6]=1.[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Br:7][C:5]1[N:6]=[C:2]([C:23]#[C:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:3][C:4]=1[C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 58227559(2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone

Produkt 1

HCID 58227508(4-Bromo-2-phenylethynyl-thiazol-5-yl)-piperidin-1-yl-methanoneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of a mixture of intermediate 49 (2,4-Dibromo-thiazol-5-yl)-piperidin-1-yl-methanone (325 mg, 0.918 mmol), bis(triphenylphosphine)palladium(II) chloride (12.9 mg, 0.0184 mmol), copper(I) iodide (8.74 mg, 0.0459 mmol) and phenylacetylene (0.101 mL, 0.918 mmol) was added triethylamine (3.0 mL, 22 mmol) and the reaction was heated at 90° C. for 30 minutes in a microwave (150 watts). The solvent triethylamine was removed and the crude product was extracted with dichloromethane and washed the organic portion with aqueous citric acid solution, water and brine. Purification of the crude product afford the titled compound (4-Bromo-2-phenylethynyl-thiazol-5-yl)-piperidin-1-yl-methanone (60 mg, 20%) as a pale brown color solid

Aufarbeitung

  1. customThe solvent triethylamine was removed
  2. extractionthe crude product was extracted with dichloromethane
  3. washwashed the organic portion with aqueous citric acid solution, water and brine
  4. customPurification of the crude product

Quellen und Nachweise

ORD-Eintrag
ord-d8e38c0e5a4f490b8b10118b77ebb566
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440837B2

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