Imidazole → 1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine

Participants

Reaction Steps

To a suspension of 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropan-1-ol (Preparation 66, 3.86 g, 12.2 mmol) in DCM (50 mL) was added imidazole (2.08 g, 30.5 mmol) followed by TBDMSCl (2.21 g, 14.7 mmol) and the reaction was stirred at room temperature for 18 hours. The reaction was partitioned between water (30 mL) and DCM (40 mL). The aqueous layer was washed twice with DCM (40 mL), the organic layers combined, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 30% EtOAc in heptanes followed by 80:20:2 EtOAc:MeOH:NH3 to afford the title compound as a colourless oil (3.90 g, 74%).

Provenance & Evidence