Diisopropylethylamine → 1-(6-Bromopyridin-2-yl)-1,4-diazepan-6-ol

HRID 57897

Reaktionsgleichung

Reaktionsgleichung von HRID 57897
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[NH:9]1[CH2:15][CH:14]([OH:16])[CH2:13][NH:12][CH2:11][CH2:10]1.CCN(C(C)C)C(C)C>C(O)C>[Br:1][C:2]1[N:3]=[C:4]([N:9]2[CH2:15][CH:14]([OH:16])[CH2:13][NH:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 211142751,4-Diazepan-6-ol

Produkt 1

HCID 867070881-(6-Bromopyridin-2-yl)-1,4-diazepan-6-olAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-bromo-6-fluoropyridine (477 mg, 2.7 mmol), 1,4-diazepan-6-ol (350 mg, 3 mmol), and DIPEA (1.94 g, 15 mmol) in ethanol (10 mL) was heated at 100° C. for 16 hours. After it was cooled, the reaction mixture was concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL) and washed with brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 1-(6-bromopyridin-2-yl)-1,4-diazepan-6-ol as a colorless oil (400 mg, 48.9%). MS (ESI) m/z: 272 [M+H]+.

Aufarbeitung

  1. temperatureAfter it was cooled
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc (100 mL)
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4a05fc6b800647e6bfba96bdba62fac7
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

Verknüpfte Notizen

Wird geladen…