Reaktion #1715306

Reaktionsgleichung

2-(4-(1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol

NBS

→

2-(4-(7-bromo-1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol

Ausbeute 18.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated under reduced pressure
2. 2
   Sonstigethe residue was purified by flash chromatography (40 g silica gel column; gradient elution with 0 to 50% EtOAc/heptane)

Vorschrift

To a solution of 2-(4-(1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.755 g, 1.63 mmol, Preparation #AX.1) in DCM (16.3 ml) at about −20° C. was added NBS (0.462 g, 2.59 mmol). The resulting suspension was allowed to stir at about −20° C. for about 15 min. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (40 g silica gel column; gradient elution with 0 to 50% EtOAc/heptane) to give 2-(4-(7-bromo-1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.11 g, 18%). LC/MS (Table 2, Method a) Rt=2.41 min; MS m/z 385 (M+H)+. Syk IC50=B.

Quelle