Sodium Azide → HCID 58128600, compound

Participants

Reaction Conditions

Reaction Steps

5-Iodo-2-(4′-methoxybenzyloxy)pyridine from step 1 of this example (682 mg, 2.0 mmol), sodium azide (260 mg, 4.00 mmol), copper (1) iodide (38.1 mg, 0.200 mmol) and L-ascorbic acid sodium salt (19.81 mg, 0.100 mmol) were added to a sealable high pressure vessel. The vessel was evacuated and purged with nitrogen, then ethanol (2.75 ml) and water (1.25 ml) were added. N,N-dimethylethylenediamine (31.9 μl, 0.300 mmol) was then added via microliter syringe. The top was sealed and the reaction heated to 100° C. A safety shield was placed in front of the reaction as a precaution. After 90 minutes, the reaction was cooled to room temperature. Reaction was judged to be complete by TLC, so the reaction was partitioned between ethyl acetate and water. The aqueous was extracted again with ethyl acetate, and the combined organics washed again with water. The organic layer was dried over sodium sulfate, filtered and evaporated to give the crude product. The material was purified by column chromatography on a Biotage 40 g SiO2 column, eluting with 5-25% ethyl acetate/heptane to give the title compound as a light tan solid.

Provenance & Evidence