Biphenyl-2-boronic acid → 2-biphenyl-2-yl-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

HRID 1454970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454970
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1.[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O>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>[C:21]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][C:10](=[O:20])[C:11]=2[C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[F:19])[N:7]=1

Komponenten

4

Edukt 2

HCID 4589187Biphenyl-2-boronic acidHCID 575312262-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

Produkt 1

HCID 167499582-biphenyl-2-yl-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2-chloro-5-(2,6-difluorophenyl)-6H-pyrido[1,2-b]pyridazin-6-one (50 g, 0.17 mmol), biphenyl-2-ylboronic acid (51.4 mg, 0.26 mmol), and Tetrakis (19.6 g, 0.017 mmol) were added to a flask and purged with N2 (3×). After the addition of toluene (5 mL), ethanol (0.5 mL), and 2M Na2CO3 (0.5 mL) the resulting mixture was heated to 90° C. for 1 hour. The reaction was concentrated in vacuo and the crude residue was dissolved in H2O/EtOAc (1:1) and extracted with H2O, 1N HCl (2×), brine (2×), dried over MgSO4, and concentrated in vacuo to yield an oil. The crude material was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH) to yield the title compound.

Aufarbeitung

  1. custompurged with N2 (3×)
  2. additionAfter the addition of toluene (5 mL), ethanol (0.5 mL), and 2M Na2CO3 (0.5 mL) the resulting mixture
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionthe crude residue was dissolved in H2O/EtOAc (1:1)
  5. extractionextracted with H2O, 1N HCl (2×), brine (2×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto yield an oil
  9. customThe crude material was purified via silica gel chromatography (CH2Cl2/EtOAc/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-daa5d0327c964cf583f641bb8b90e033
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07482345B2

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