Sodium Carbonate → 4-(3-Phenylimidazo[1,2-a]pyridin-7-yl)benzaldehyde

HRID 1245478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245478
I[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Li+]>O1CCOCC1>[C:19]1([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]4[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=4)=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic Acid2×HCID 433294Lithium ChlorideHCID 219128644-(3-Iodoimidazo[1,2-a]pyridin-7-yl)benzaldehyde

Produkt 1

HCID 219128614-(3-Phenylimidazo[1,2-a]pyridin-7-yl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphoine)palladium(0) (92 mg, 0.080 mmol, 0.050 equiv) was added to a deoxygenated mixture of 4-(3-iodoimidazo[1,2-a]pyridin-7-yl)benzaldehyde (2-4, 555 mg, 1.94 mmol, 1 equiv), phenyl boronic acid (486 mg, 3.99 mmol, 2.50 equiv), and aqueous saturated sodium carbonate solution (2.4 mL, 3.0 equiv) in dioxane (20 mL), and the resulting mixture was heated at reflux for 4 h. Additional tetrakis(triphenylphosphoine)palladium(0) (100 mg, 0.09 mmol, 0.05 equiv), phenyl boronic acid (500 mg, 4.0 mmol, 2.5 equiv), aqueous saturated sodium carbonate solution (2.5 mL, 3.1 equiv), and lithium chloride (200 mg, 5 mmol, 3 equiv) were added and the mixture was heated at reflux for 18 h. The reaction mixture was cooled, then concentrated, and the residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (6×100 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA) to give 4-(3-phenylimidazo[1,2-a]pyridin-7-yl)benzaldehyde (2-5) as a tan solid. LRMS m/z (M+H) Calcd 299.3, found 298.9.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 18 h
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated
  7. customthe residue was partitioned between half-saturated aqueous NaCl solution (100 mL) and EtOAc (6×100 mL)
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by reverse-phase liquid chromotography (H2O/CH3CN gradient w/0.1% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-98944097f0ca4bb890d50fa2fdc49477
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125888B2

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