Diisobutylaluminum hydride → (6-Amino-5-iodopyridin-3-yl)methanol

Participants

Reaction Steps

A solution of methyl 6-amino-5-iodonicotinate (335 mg, 1.205 mmol) in dichloromethane (18 mL) was added DIBAL (1.5 M in toluene, 1.61 mL, 2.41 mmol) via syringe dropwise at 0° C. The reaction was monitored by LC_MS, and added more DIBAL (0.8 mL, 1.2 mmol) to drive the reaction to complete. The reaction was quenched with addition of MeOH (1 mL) dropwise at 0° C., stirred at rt for 2 h and filtered through a CELITE® pad, rinsed with ethyl acetate and dichloromethane. The organic layers were combined and concentrated onto SiO2 which was purified by a flash column using 50%, 80% and 100% ethyl acetate in heptane as an eluent to give the product (204 mg, 68 mmol).

Provenance & Evidence