N-bromobutanimide → 3-(Benzyloxy)-5-bromopyridin-2-amine

HRID 1426081

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([NH2:15])=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

3-(Benzyloxy)pyridin-2-amine (25.0 g, 124.9 mmol) was added to acetonitrile (300 mL) and cooled to 0° C. 1-Bromopyrrolidine-2,5-dione (22.22 g, 124.9 mmol) was added portionwise and the reaction mixture was stirred for 15 minutes, then concentrated to dryness. The residue was dissolved in EtOAc and partitioned with water. The organic layer was washed twice with saturated sodium bicarbonate and once with brine. Activated charcoal was added to the organic layer, and the organic layer was warmed to reflux, then cooled, filtered through a plug of celite, and concentrated to give 9.4 g of the title compound. The celite and charcoal were resuspended in EtOAc and filtered through a celite plug to give an additional 3.6 g of the title compound, to provide a total of 12.0 g (34.3% yield). 1H NMR (CDCl3) δ 7.74 (d, 1H), 7.41 (m, 5H), 7.08 (d, 1H), 5.04 (s, 2H), 4.74 (bs, 2H). Mass spectrum (apci) m/z=279.1 (M+H).

Aufarbeitung

concentrationconcentrated to dryness
dissolutionThe residue was dissolved in EtOAc
custompartitioned with water
washThe organic layer was washed twice with saturated sodium bicarbonate and once with brine
additionActivated charcoal was added to the organic layer
temperaturethe organic layer was warmed
temperatureto reflux
temperaturecooled
filtrationfiltered through a plug of celite
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-4f044eb2a0fc46f1b1e3b928467269a7
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08933077B2

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