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% and100% ethyl acetate in heptane as an eluent to give the product (204 mg, 68 mmol).

Provenance & Evidence