N-bromobutanimide → HCID 178489113, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.264 g, 0.949 mmol; Example #AU.1.1) in DMF (3 mL) was added NBS (0.169 g, 0.949 mmol). The mixture was allowed to stir at about rt for about 16 h. Additional NBS (0.085 mg, 0.478 mmol) was added and the mixture was heated to about 50° C. for about 3 h. The mixture was purified by flash chromatography (40 g silica gel column, 10 to 100% EtOAc/heptane) to give 8-bromo-3-(4-methoxyphenyl)-1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.150 g, 44%). LC/MS (Table 2, Method a) Rt=2.35 min.; MS m/z: 357 (M+H)+. Syk IC50=A.

Provenance & Evidence