Dichloromethane → HCID 58382176, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with NaH (60 wt % in mineral oil, 0.025 g, 0.64 mmol) in DMF (2.0 mL). The suspension was cooled to about 0° C., followed by the addition of a solution of tert-butyl (7-bromo-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamate (0.16 g, 0.49 mmol) in DMF (2.0 mL). The mixture was stirred at about 0° C. for about 10 min and then at rt for about 20 min. The mixture was cooled to about 0° C. followed by the addition of a solution of TsCl (0.112 g, 0.587 mmol) in DMF (1.0 mL). The mixture was stirred at 0° C. for about 20 min and warmed to rt and stirred for about 1 h. To the mixture were added DCM (10 mL) and water (10 mL). The organic layer was isolated and dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. EtOAc (10 mL) and heptane (10 mL) were added and then the mixture was concentrated under reduced pressure to give tert-butyl (7-bromo-5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamate (0.24 g, 91%): LC/MS (Table 2, Method c) Rf=1.59 min; MS m/z 481 (M+H)+.

Provenance & Evidence