Trifluoroacetic acid → (4-Chloro-benzyl)-(6-chloro-pyridin-2-yl)-amine

HRID 1367359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367359
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:6][C:7]=1F.[Cl:18]C1C=CC(C=O)=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:5]2[CH:4]=[CH:3][CH:2]=[C:7]([Cl:18])[N:6]=2)=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 77264-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 57619198(5-Bromo-6-fluoro-pyridin-2-yl)-(4-chloro-benzyl)-amine

Produkt 1

HCID 57619237(4-Chloro-benzyl)-(6-chloro-pyridin-2-yl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To 6-chloro-pyridin-2-ylamine (537, 5.60 g, 0.0436 mol) in acetonitrile (300 mL) were added 4-chlorobenzaldehyde (40, 6.7 g, 0.048 mol), trifluoroacetic acid (13 mL, 0.17 mol) and triethylsilane (21 mL, 0.13 mol). The reaction was heated to reflux for 4 hours, then concentrated, poured into water, extracted with ethyl acetate, and washed with sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The filtrate was purified with silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give a white solid (538, 6.5 g, 59%). MS (ESI) [M+H+]+=255.1.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washwashed with sodium bicarbonate and brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe filtrate was purified with silica gel column chromatography
  11. washeluting with 20% to 100% ethyl acetate in hexane
  12. customto give a white solid (538, 6.5 g, 59%)

Quellen und Nachweise

ORD-Eintrag
ord-b360518a28e1447587896411dab81a52
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893075B2

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