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3-Bromoaniline → 4'-Cyano-3'-fluoro-biphenyl-3-ylamine

HRID 240151
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 240151
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[F:12])#[N:2].Br[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:14]2[CH:20]=[CH:19][CH:18]=[C:16]([NH2:17])[CH:15]=2)=[CH:5][C:4]=1[F:12])#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 115623-BromoanilineHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2783130(4-Cyano-3-fluorophenyl)boronic acid

Produkt 1

HCID 668657734'-Cyano-3'-fluoro-biphenyl-3-ylamineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

4-cyano-3-fluorophenyl boronic acid (0.144 g, 0.872 mmol) and 3-bromoaniline (0.063 mL, 0.581 mmol) were combined in dioxane (2 mL) in a flame-dried, round-bottom flask. K3PO4 (1.27M, 0.778 mL, 0.99 mmol), PCy3 (0.004 g, 0.014 mmol), and Pd2(dba)3 (0.005 g, 0.006 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in CH2Cl2. The organic phase was dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by flash silica column chromatography (5-60% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.120 g in 98% yield.

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by flash silica column chromatography (5-60% EtOAc/hexanes)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.120 g in 98% yield

Quellen und Nachweise

ORD-Eintrag
ord-bd7ff1da9a5946eb91decae9aee1c007
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642788B2

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