Sodium Carbonate → N-[5-(2,4-difluorophenyl)-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamide

HRID 255115

Reaktionsgleichung

Reaktionsgleichung von HRID 255115
Cl[C:2]1[S:6][C:5](=[N:7][C:8](=[O:10])[CH3:9])[N:4]([CH2:11][CH2:12][O:13][CH3:14])[CH:3]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C(O)C.C(OCC)(=O)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>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C:2]1[S:6][C:5](=[N:7][C:8](=[O:10])[CH3:9])[N:4]([CH2:11][CH2:12][O:13][CH3:14])[CH:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 66858991N-[5-chloro-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamide

Produkt 1

HCID 66860261N-[5-(2,4-difluorophenyl)-3-(2-methoxyethyl)-1,3-thiazol-2(3H)-ylidene]acetamideAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 86587095Dimethoxyethane ethanol waterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A flask was charged with the product from Example 120A (10.2 g, 42.6 mmol), 2,4-difluorophenylboronic acid (8.08 g, 51.1 mmol), Na2CO3 (64.0 mL of a 2 M aqueous solution, 128 mmol) and PdCl2(PPh3)2 (1.5 g, 2.13 mmol) in 100 mL of DME/H2O/ethanol (7:3:2). The mixture was warmed to 85° C. and stirred overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water. The organic extract was dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate:hexane to provide 11.5 g (86%) of the title compound: 1H NMR (300 MHz, CDCl3) δ 2.17 (s, 3 H) 3.27 (s, 3 H) 3.71 (t, J=5.3 Hz, 2 H) 4.37 (t, J=5.4 Hz, 2 H) 7.17-7.24 (m, 1 H) 7.38-7.48 (m, 1 H) 7.64-7.74 (m, 1 H) 7.88 (s, 1 H); MS (ESI+) m/z 313 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on SiO2 using a gradient of 0% to 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-daaa0fbe867a48e7b98bffb6b7f23aae
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875639B2

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