Sodium Carbonate → 4-Chloro-2-(2,6-dichloro-4-vinyl-phenyl)-thiazolo[5,4-c]pyridine

HRID 2366221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366221
[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][C:14](I)=[CH:13][C:12]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:28][CH2:27]1>O.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>[Cl:1][C:2]1[C:7]2[S:8][C:9]([C:11]3[C:16]([Cl:17])=[CH:15][C:14]([CH:27]=[CH2:28])=[CH:13][C:12]=3[Cl:19])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 866689974-Chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine

Produkt 1

HCID 867233104-Chloro-2-(2,6-dichloro-4-vinyl-phenyl)-thiazolo[5,4-c]pyridineAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 4-chloro-2-(2,6-dichloro-4-iodo-phenyl)-thiazolo[5,4-c]pyridine (0.30 g, 0.68 mmol), vinyl borane pinacol ester (0.105 g, 0.68 mmol), PdCl2(PPh3)2 (0.029 g, 0.04 mmol) and sodium carbonate (0.288 g, 2.70 mmol) in water (0.4 mL) and dioxane (4 mL) was degassed with nitrogen and heated at 100° C. for 2 hours. The reaction mixture was cooled to room temperature and then partitioned between EtOAc and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 0-8% EtOAc in pentane to give the desired compound as an off-white solid (0.168 g, 72% yield). 1H NMR (300 MHz, CDCl3): δ 8.51 (d, J=5.6 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.53-7.45 (m, 2H), 6.69-6.62 (m, 1H), 5.91 (d, J=17.5 Hz, 1H), 5.52 (d, J=10.9 Hz, 1H).

Aufarbeitung

  1. customwas degassed with nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between EtOAc and water
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluting with 0-8% EtOAc in pentane

Quellen und Nachweise

ORD-Eintrag
ord-1b47c98866ce4419a06f635b8bf34199
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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