Diisobutylaluminum hydride → HCID 58207932, compound

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).

1. customthe reaction
2. customThe reaction was quenched with addition of MeOH (1 mL) dropwise at 0° C.
3. filtrationfiltered through a CELITE® pad
4. washrinsed with ethyl acetate and dichloromethane
5. concentrationconcentrated onto SiO2 which
6. customwas purified by a flash column

ORD record

ord-84a7323f613d4489ad5991d26b25aff2

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08410128B2