Trifluoroacetic acid → 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-amine

Participants

Reaction Conditions

Reaction Steps

In a flask was added tert-butyl 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylcarbamate (0.200 g, 0.382 mmol) and TFA (0.088 mL, 1.15 mmol) in DCM (1 mL). The mixture was stirred for about 2 h at about 30° C. Additional TFA (0.100 mL, 1.29 mmol) was added and the mixture was stirred at about 40° C. overnight. The mixture was diluted with EtOAc (10 mL) and washed with saturated aqueous Na2CO3 (5 mL) and dried over MgSO4, filtered and concentrated in vacuo. The material was purified by 4 g silica column eluting with 10 to 100% EtOAc/DCM to provide 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-amine (0.065 g, 40%): LC/MS (Table 2, c) Rt=1.62 min; MS m/z 424 (M+H)+.

Provenance & Evidence