Water → ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate

HRID 1799114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1799114
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][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[C:19]#[CH:20].C(N(CC)CC)C.O>C1COCC1.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>[C:7]1([C:5]2[S:6][C:2]([C:20]#[C:19][CH2:18][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 44558337Ethyl 5-bromo-2-phenylthiazole-4-carboxylate

Produkt 1

HCID 67425248ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Nitrogen was bubbled through a solution of Ethyl 5-bromo-2-phenylthiazole-4-carboxylate (3.6 g, 11.5 mmol) and 2-(prop-2-ynyloxy)tetrahydro-2H-pyran (3.3 mL, 23.1 mmol) in THF (30 mL). Dichlorobis(triphenylphosphine)palladium (II) (405 mg, 0.6 mmol), copper (I) iodide (55 mg, 0.3 mmol), and triethylamine (TEA) (8 mL, 57.7 mmol) were added and the reaction mixture was heated at 100° C. for 30 min in a microwave reactor. The reaction mixture was poured into H2O and extracted with EtOAc. 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 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate (3.8 g, 88% yield).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by MPLC
  6. washeluting with pentane/EtOAc (0-50% gradient)

Quellen und Nachweise

ORD-Eintrag
ord-75ab3da032454e33b3d36100f27ca28b
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343997B2

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