Nitrogen → HCID 22648856, Verbindung

HRID 393275

Reaktionsgleichung

Reaktionsgleichung von HRID 393275
N#N.Br[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([CH3:11])[CH:5]=1.[CH:12]([C:14]1[O:15][C:16](B(O)O)=[CH:17][CH:18]=1)=[O:13].C([O-])([O-])=O.[Na+].[Na+]>CC#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:10][C:7]1[CH:8]=[CH:9][C:4]([C:16]2[O:15][C:14]([CH:12]=[O:13])=[CH:18][CH:17]=2)=[CH:5][C:6]=1[CH3:11]

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 168964-Bromo-2-methylphenolHCID 27343555-Formylfuran-2-boronic acid

Produkt 1

HCID 22648856HCID 22648856, VerbindungAusbeute 47,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Pd(PPh3)4 (69.3 mg, 0.06 mmol) was added to a degassed (N2 for 15 min) solution of 4-bromo-2-methylphenol (225 mg, 1.20 mmol), 2-formylfuran-5-boronic acid (177 mg, 1.26 mmol) and aqueous 0.4 M Na2CO3 (6 mL) in MeCN (12 mL). The mixture was heated to reflux for 12 h. The hot mixture was filtered and the cake was washed with MeCN (6 mL). The filtrate was concentrated to half the volume and was diluted with EtOAc. The resulting solution was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (Hexane:EtOAc, 7:3) to provide the title compound (115 mg, 47% yield) as a yellow solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 h
  3. filtrationThe hot mixture was filtered
  4. washthe cake was washed with MeCN (6 mL)
  5. concentrationThe filtrate was concentrated to half the volume
  6. additionwas diluted with EtOAc
  7. washThe resulting solution was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash chromatography (Hexane:EtOAc, 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-b1aa848caddb427ab02d298633b3ab7b
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806265B2

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