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

HRID 57843

Reaktionsgleichung

Reaktionsgleichung von HRID 57843
[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) in ethanol (10 mL) was heated at 100° C. for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted with EtOAc (100 mL). The solution was washed with brine, 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. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with EtOAc (100 mL)
  3. washThe solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c81de5258514889bd3738db16a79614
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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