Sodium hydride → 6-Bromo-1,2-dihydro-3H-pyrrolo[1,2-c]imidazol-3-one

HRID 1056297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056297
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][NH2:8])[NH:5][CH:6]=1.N1([C:14](N2C=CN=C2)=[O:15])C=CN=C1.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:7][NH:8][C:14](=[O:15])[N:5]2[CH:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 56828153(4-bromo-1H-pyrrol-2-yl)methanamine

Produkt 1

HCID 897938476-Bromo-1,2-dihydro-3H-pyrrolo[1,2-c]imidazol-3-oneAusbeute 36,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (4-bromo-1H-pyrrol-2-yl)methanamine (Enamine, Ltd., Kiev, Ukraine; 57.7 mg, 0.330 mmol), di(1H-imidazol-1-yl)methanone (CDI; Aldrich; 58.8 mg, 0.363 mmol), and NaH (60% wt. in mineral oil; 15.8 mg, 0.396 mmol) in THF (3.0 mL) was stirred under argon at 23° C. for 15 min. The reaction mixture was subsequently concentrated onto silica gel and chromatographically purified (silica gel, 0-60% EtOAc/hexanes) to provide 6-bromo-1H-pyrrolo[1,2-c]imidazol-3(2H)-one (23.9 mg, 0.119 mmol, 36% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.58 (1H, br. s.), 7.29 (1H, s), 6.16 (1H, d, J=1.2 Hz), 4.35 (2H, s). m/z (ESI, +ve) 200.9/202.9 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was subsequently concentrated onto silica gel
  2. customchromatographically purified (silica gel, 0-60% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8f3b8eff06cc4735a512f3424694b47b
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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