Trifluoroacetic acid → 6-Bromo-5-fluoropyridin-2-amine

HRID 1396478

Reaktionsgleichung

Reaktionsgleichung von HRID 1396478
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:15][C:10]1[N:9]=[C:8]([NH2:7])[CH:13]=[CH:12][C:11]=1[F:14]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71744124Tert-butyl (6-bromo-5-fluoropyridin-2-YL)carbamate

Produkt 1

HCID 596058336-Bromo-5-fluoropyridin-2-amineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (6-bromo-5-fluoro-pyridin-2-yl)-carbamic acid tert-butyl ester (1.43 g, 4.91 mmol) in DCM (25 mL) was added TFA (3.78 mL, 49.1 mmol, Eq: 10.0). The mixture was stirred at room temperature for 2 h, after which it was concentrated in vacuo, and redissolved in EtOAc. The organic layer was washed with sat. aq. NaHCO3 followed by water and brine. The resulting organic layer was concentrated on to silica gel and chromatographed (10% to 40% EtOAc/hexanes) to give 6-bromo-5-fluoro-pyridin-2-ylamine (850 mg, 91%). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.23 (dd, J=8.6, 7.5 Hz, 1H), 6.41 (dd, J=8.6, 2.6 Hz, 1H), 4.40 (br. s, 2H).

Aufarbeitung

  1. concentrationafter which it was concentrated in vacuo
  2. dissolutionredissolved in EtOAc
  3. washThe organic layer was washed with sat. aq. NaHCO3
  4. concentrationThe resulting organic layer was concentrated on to silica gel
  5. customchromatographed (10% to 40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cc36f01cdd014233bd45c2777bbfdcf9
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901124B2

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