Sodium hydride → (6S)-6-[(5-Bromopyridin-3-yl)methoxy]-2-nitro-6,7-dihydro-5H-imi-dazo[2,1-b][1,3]oxazine

HRID 1446075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446075
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][C@H:9]([OH:13])[CH2:8][O:7]2)([O-:3])=[O:2].Cl.[Br:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH2:22]Cl)[CH:21]=1.[H-].[Na+]>CN(C=O)C>[Br:15][C:16]1[CH:21]=[C:20]([CH2:22][O:13][C@@H:9]2[CH2:8][O:7][C:6]3=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][N:11]3[CH2:10]2)[CH:19]=[N:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 10130259(S)-2-nitro-6,7-dihydro-5H-imidazo(2,1-b)(1,3)oxazin-6-olHCID 125150693-Bromo-5-(chloromethyl)pyridine hydrochloride

Produkt 1

HCID 49851940(6S)-6-[(5-Bromopyridin-3-yl)methoxy]-2-nitro-6,7-dihydro-5H-imi-dazo[2,1-b][1,3]oxazineAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxa-zin-6-ol (3.63 g, 19.6 mmol) and 3-bromo-5-(chloromethyl)pyridine hydrochloride (4.78 g, 19.6 mmol, 1 eq) in dry DMF (80 mL) was treated with NaH (1.88 g, 47 mmol, 2.4 eq, 60% in mineral oil) at 0-5° C., then stirred at room temperature overnight (16 h), quenched with water (150 mL), and extracted into EtOAc. Chromatography of the crude product on silica gel, eluting with MeOH/CH2Cl2 (1:19), gave the title product (2.10 g, 30%) as white solid. APCI MS m/z 355.7, 357.7 (M+H). 1H NMR (400 MHz, (CD3)2SO) δ 8.64 (d, J=2.3 Hz, 1H), 8.52 (d, J=1.7 Hz, 1H), 8.03 (s, 1H), 7.97 (br t, J=2.1 Hz, 1H), 4.73 (d, J=12.6 Hz, 1H), 4.70-4.65 (m, 2H), 4.48 (d, J=12 Hz, 1H), 4.31-4.20 (m, 3H).

Aufarbeitung

  1. customquenched with water (150 mL)
  2. extractionextracted into EtOAc
  3. washChromatography of the crude product on silica gel, eluting with MeOH/CH2Cl2 (1:19)

Quellen und Nachweise

ORD-Eintrag
ord-b610238280934b3aa9a5723d9a173733
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666864B2

Notizen zur Reaktion

Wird geladen…