Trifluoroacetic acid → [4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

HRID 878071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 878071
C(OC(=O)[N:7]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[CH2:8][C:9]([F:12])([F:11])[F:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1[NH:7][CH2:8][C:9]([F:12])([F:10])[F:11]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 70663661[4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 70663252[4-(2-Chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of [4-(2-chloro-phenyl)-pyridin-3-yl]-(2,2,2-trifluoro-ethyl)-carbamic acid tert-butyl ester (120 mg, 310 μmol) in CH2Cl2 (2 mL) at 0° C. was added TFA (2 mL). The reaction mixture was stirred at room temperature for 2 hours and then concentrated under vacuum. The residue was extracted with 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc. The layers were separated and the aqueous layer was extracted a second time with 30 mL EtOAc. The combined organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. Light yellow solid (79 mg, 89%). MS (ESI): m/z=287.055 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. extractionThe residue was extracted with 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted a second time with 30 mL EtOAc
  5. washThe combined organic layers were washed with 30 mL brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-edcd39856e724c76bbc34199a3adbe12
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987307B2

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