Sodium hydride → 2-bromo-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine

Participants

Reaction Steps

2-Bromo-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine (0.500 g, 1.40 mmol) in DMF (15 mL) was cooled to about 0° C. then treated with NaH (60% dispersion in mineral oil, 0.112 g, 2.80 mmol). The mixture was stirred for about 15 min, SEM-Cl (0.372 mL, 2.10 mmol) was added, and the mixture was warmed to ambient temperature for about 15 min. The mixture was concentrated and purified by silica gel chromatography (40 g silica column) eluting with DCM to give 2-bromo-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.61 g, 89%): LC/MS (Table 2, Method a) Rt=3.88 min; MS m/z: 489 (M+H)+.

Provenance & Evidence