Water → Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate

HRID 453294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453294
Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18]([O:21][CH3:22])[C:19]#[CH:20].O>C(COC)OC.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>[CH3:22][O:21][CH2:18][C:19]#[C:20][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

7

Edukt 3

HCID 962WaterHCID 693933-MethoxypropyneHCID 44558337Ethyl 5-bromo-2-phenylthiazole-4-carboxylate

Produkt 1

HCID 67425118Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Nitrogen was bubbled through a solution of Ethyl 5-bromo-2-phenylthiazole-4-carboxylate (13.1 g, 41.9 mmol) and methyl propargyl ether (7.1 mL, 83.9 mmol) in dimethoxyethane (DME) (200 mL). Dichlorobis(triphenylphosphine)palladium (II) (1.47 g, 2.2 mmol), copper (I) iodide (0.2 g, 1.1 mmol), and TEA (29 mL, 210 mmol) were added and the reaction mixture was heated at reflux for 16 h. The reaction mixture was cooled to room temperature, poured into H2O (200 mL) and extracted with EtOAc (2×200 mL). The combined organics were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-50% gradient) to give ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate as a tan solid (11 g, 88% yield).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with EtOAc (2×200 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by MPLC
  8. washeluting with pentane/EtOAc (0-50% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-03e0f68d12a94b91a1020548faf62a2f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492401B2

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