Sodium Carbonate → HCID 67399195, Verbindung

HRID 471598

Reaktionsgleichung

Reaktionsgleichung von HRID 471598
I[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].[CH:13](/B(O)O)=[CH:14]\[CH3:15].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O.CCOC(C)=O>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:2](/[CH:13]=[CH:14]/[CH3:15])[C:3]=1[C:4]#[N:5])([O-:12])=[O:11]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 24971989HCID 24971989, Verbindung

Produkt 1

HCID 67399195HCID 67399195, VerbindungAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 2-iodo-6-nitrobenzonitrile (Example 130d) (1.52 g, 5.53 mmol), tetrakis(tiphenylphosphine)palladium(0) (0.64 g, 0.55 mmol), trans-1-propen-1-ylboronic acid (0.95 g, 11.06 mmol), sodium carbonate (0.65 g, 6.08 mmol) and water (10.0 mL) in dimethoxyethane (DME) (40.0 mL) was heated at reflux for 15 h, under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with water (20 mL) and EtOAc (100 mL). The organic phase was separated and the aqueous phase was extracted with EtOAc (3×50 mL). The combined extract was washed with brine and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (7:3), to give 0.98 g (94%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 8.16-8.24 (m, 2H), 7.83-7.89 (m, 1H), 6.71-6.84 (m, 2H), 1.90-2.02 (m, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 15 h, under a nitrogen atmosphere
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with EtOAc (3×50 mL)
  5. extractionThe combined extract
  6. washwas washed with brine
  7. dry with materialdried with anhydrous MgSO4
  8. customThe filtrate was evaporated
  9. customthe residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (7:3)

Quellen und Nachweise

ORD-Eintrag
ord-f5085f93e9574224a1bdf498b7591d2f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633186B2

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