Nitrogen → 4'-Formyl-3-biphenylcarboxamide

HRID 70325

Reaktionsgleichung

Reaktionsgleichung von HRID 70325
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH2:10][C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)=[O:12].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].N#N>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:11]([NH2:10])=[O:12])[CH:18]=2)=[CH:3][CH:4]=1)=[O:7]

Komponenten

8

Edukt 5

HCID 947NitrogenHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 2737814(3-Carbamoylphenyl)boronic acid

Produkt 1

HCID 593165294'-Formyl-3-biphenylcarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromobenzaldehyde (2.78 g; 15.0 mmol), [3-(aminocarbonyl)-phenyl]boronic acid (2.72 g; 16.5 mmol), PdCl2(dppf).CH2Cl2 (0.306 g; 0.38 mmol), DME (25 mL) and Na2CO3 (25 mL of a 2M solution) was sparged 20 min with N2 and heated under reflux for 90 min (consumption of aryl bromide observed by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated, and the aqueous layer was extracted with EtOAc (×2). Combined organics were washed (H2O, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a tan solid. LC/MS (method A) 1.91 min, m/z 226 (M+H).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 90 min
  3. custom(consumption of aryl bromide observed by LC/MS)
  4. temperatureUpon cooling
  5. customthe mixture was partitioned between EtOAc/H2O, layers
  6. customwere separated
  7. extractionthe aqueous layer was extracted with EtOAc (×2)
  8. washCombined organics were washed (H2O, brine)
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f16869d2600a431382fa4e227ab303ab
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822518B2

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