N-Iodosuccinimide → 4-bromo-3-iodo-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 331010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 331010
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[CH:10][C:3]=12.C1C(=O)N([I:19])C(=O)C1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[C:10]([I:19])[C:3]=12

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 529877864-Bromo-2-methyl-1H-pyrrolo(2,3-b)pyridine

Produkt 1

HCID 710901934-bromo-3-iodo-2-methyl-1H-pyrrolo[2,3-b]pyridineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 4-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (D24) (1.65 g, 7.82 mmol) in DCM (70 mL) was added NIS (1.935 g, 8.60 mmol) at 0° C. and the mixture was stirred for 1.5 hour at 0° C. The mixture was evaporated in vacuo. DCM (ca. 20 mL) was added to the residue. The formed precipitate was filtered, rinsed with DCM to give the title compound (2.45 g). LCMS (A): m/z (M+H)+ 337/339, C8H6BrIN2 requires 336/338 (acidic).

Aufarbeitung

  1. customThe mixture was evaporated in vacuo
  2. additionDCM (ca. 20 mL) was added to the residue
  3. filtrationThe formed precipitate was filtered
  4. washrinsed with DCM

Quellen und Nachweise

ORD-Eintrag
ord-864ac5436dfa4d54a94e5208c668edf3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877742B2

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