N-bromobutanimide → HCID 67353647, Verbindung

HRID 1478903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478903
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[N:8]=[CH:7][C:6]=2[CH:5]=[CH:4]1)[CH3:2].C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[Br:23][C:5]1[C:6]2[CH:7]=[N:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:11]=2[N:3]([CH2:1][CH3:2])[CH:4]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 67354512HCID 67354512, Verbindung

Produkt 1

HCID 67353647HCID 67353647, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of methyl 1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (IF, 700 mg, 3.43 mmol) in DCM (5 ml) was added NBS (610 mg, 3.43 mmol). The reaction mixture was stirred at room temperature for 10 min. The reaction mixture was concentrated in vacuo and purified by chromatography (SiO2, EtOAc) to give methyl 3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridine-6-carboxylate (3A, 950 mg, 3.36 mmol, 98% yield) as a white powder. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.52 (t, J=7.33 Hz, 3 H) 4.04 (s, 3 H) 4.25 (q, J=7.33 Hz, 2 H) 7.33 (s, 1 H) 8.22 (d, J=0.76 Hz, 1 H) 8.92 (d, J=1.01 Hz, 1 H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by chromatography (SiO2, EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-3e9efdeaf122484fae22845a2d1769c4
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403819B2

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