N-Iodosuccinimide → 5-Chloro-7-iodo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1262428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1262428
[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.[I:13]N1C(=O)CCC1=O>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([I:13])[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 574160595-Chloro-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Produkt 1

HCID 667122895-Chloro-7-iodo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

5-Chloro-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (54 mg, 0.27 mmol) was dissolved in 1,2-Dichloroethane (2.0 mL and then N-Iodosuccinimide (75 mg, 0.33 mmol) was added in one portion and the reaction was stirred in a vial at 60° C. overnight. The heterogenous mixture was powdered onto silica gel (0.75 g) and purified on ISCO (12 g, 0-5% EtOAc:Hex) to afford 5-Chloro-7-iodo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (49 mg; Yield=56%) as a yellow solid. m.p. 216-220° C.; LCMS (Bruker, Fragile): 4.0 min, m/z=326; 1H-NMR (CDCl3): 8.55 (s, 1H), 6.90 (s, 1H), 2.63 (s, 3H).

Aufarbeitung

  1. custompurified on ISCO (12 g, 0-5% EtOAc:Hex)

Quellen und Nachweise

ORD-Eintrag
ord-896db0daa651471899dd8b664e39c5cd
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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