Diisopropylethylamine → tert-Butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 57863

Reaktionsgleichung

Reaktionsgleichung von HRID 57863
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[N:3]=1.[N:9]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][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:12]2[CH2:13][CH2:14][CH2:15][N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 6394382-Bromo-6-fluoropyridineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Produkt 1

HCID 70700340tert-Butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylateAusbeute 50,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-bromo-6-fluoropyridine (500 mg, 2.8 mmol), tert-butyl 1,4-diazepane-1-carboxylate (568 mg, 2.8 mmol) in DIPEA (1.83 g, 14.2 mmol) and ethanol (10 mL) was heated at 100° C. for 16 hours. After it was cooled, the solvent was removed under reduced pressure, and 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 tert-butyl 4-(6-bromopyridin-2-yl)-1,4-diazepane-1-carboxylate as a colorless oil (500 mg, 50%). MS (ESI) m/z: 356 [M+H]+.

Aufarbeitung

  1. temperatureAfter it was cooled
  2. customthe solvent was removed 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-a8c79bfab3124feab3aff312cbab4f18
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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