N-bromobutanimide → 3-bromo-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 595933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595933
[CH3:1][C:2]1([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.C1C(=O)N([Br:22])C(=O)C1>C(Cl)Cl.C(OCC)(=O)C>[Br:22][C:10]1[C:11]([NH2:14])=[N:12][CH:13]=[C:8]([C:2]2([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][CH2:7]2)[CH:9]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 1180456035-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

Produkt 1

HCID 1180457983-bromo-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To an ice cold solution of 5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (50 mg, 0.26 mmol) in DCM (5 mL) was added NBS (50.9 mg, 0.28 mmol) in two portions. The reaction mixture was stirred at ambient temperature for 40 min. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered off, and concentrated to give 3-bromo-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (70 mg, 0.26 mmol, 99% yield) as yellow color residue. LCMS (m/z): 271/273 (MH+), 0.41 min.

Aufarbeitung

  1. washwashed with water, aqueous sodium bicarbonate, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered off
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6db9f113010a4b6ab8578b077a581f68
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242996B2

Notizen zur Reaktion

Wird geladen…