N-bromobutanimide → HCID 86719393, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of (R)-tert-butyl 3-(4-amino-5-(4-((1-(pivaloyloxymethyl)-1H-1,2,3-triazol-5-yl)methoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (81) (506 mg, 0.856 mmol) in DCM (20 mL) was added NBS (167 mg, 0.942 mmol). The resulting mixture was stirred at 0° C. for 2 hr. The reaction was quenched with water and extracted with DCM (20 mL×2). The combined organic layer was dried over Na2SO4. The solvent was removed under vacuum and the residue was purified by flash chromatography (silica gel, 0 to 15% MeOH in DCM, with 0.5% TEA) to provide (R)-tert-butyl 3-(4-amino-6-bromo-5-(4-((1-(pivaloyloxymethyl)-1H-1,2,3-triazol-5-yl)methoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidine-1-carboxylate (82) (344 mg, 60%). LC-MS (ESI): m/z (M/M+2) 668.8/670.8

Provenance & Evidence