N-bromobutanimide → 6-Bromo-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester

HRID 1363300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1363300
[O:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1C(=O)N([Br:38])C(=O)C1>C(Cl)Cl>[Br:38][C:7]1[C:8]2[O:1][CH:2]=[CH:3][C:4]=2[NH:5][C:6]=1[C:9]([O:11][CH3:12])=[O:10]

Komponenten

5

Edukt 3

HCID 67184N-bromobutanimideHCID 2724141Tetrabutylammonium FluorideHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylate

Produkt 1

HCID 596486446-Bromo-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a cold solution (ice-water bath) of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (1.0 g, 6.05 mmol) in DCM (10 mL) was added TBAF (1.0 M in THF, 9.0 mL, 9.0 mmol) and NBS (1.5 g, 7.9 mmol). The resulting dark colored solution was stirred from 0° C. to rt overnight. The reaction mixture was diluted with 50 mL of CH2Cl2 and washed with water (100 mL) and brine (100 mL) and dried (Na2SO4). After filtration, the filtrate was concentrated by evaporation and the crude product was purified by silica gel chromatography (0-5% EtOAc/hexane) to afford a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 8.84 (broad, 1H, NH), 7.54 (d, J=2.2 Hz, 1H), 6.48 (d, J=1.83 Hz, 1H), 3.92 (s, 3H) ppm; m+/z 244 (100%), 246 (100%).

Aufarbeitung

  1. washwashed with water (100 mL) and brine (100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated by evaporation
  5. customthe crude product was purified by silica gel chromatography (0-5% EtOAc/hexane)
  6. customto afford a white solid

Quellen und Nachweise

ORD-Eintrag
ord-05c46f1a29ae460fbb5ba364793e2caf
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07884124B2

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