Hydrochloric Acid → HCID 58477293, compound

Participants

Reaction Conditions

Reaction Steps

Solketal 58 (23.5 g, 178 mmol) was added to a suspension of NaH (7.1 g, 178 mmol, 60 wt % dispersion in mineral oil) in THF (400 mL) cooled to 0° C. The reaction mixture was stirred at room temperature for 1 h and 6-bromopicolinic acid 57 (12 g, 59.4 mmol) was added. The reaction mixture was heated at reflux for 1.5 h. After cooling to room temperature, H2O (50 mL) was added and the pH was adjusted to 3 by the addition of 3 N HCl. The mixture was poured into brine and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated. The crude product was recrystallized from pentane/EtOAc to give 59 (10 g, 66% yield). The acetonide protecting group could be removed after coupling with the appropriate aniline by treatment with EtOH/3 N HCl (4:1) at reflux for 12 h. The acetonide protecting group could be removed after coupling with the appropriate aniline by treatment with EtOH/3 N HCl (4:1) at reflux for 12 h.

Provenance & Evidence