tert-Butanol → HCID 67486075, compound

Participants

Reaction Conditions

Reaction Steps

A 500 mL flask was charged with 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)picolinic acid (10.0 g, 22.2 mmol), 2-methylpropan-2-ol (11.6 mL, 133 mmol), triethylamine (4.0 mL, 28.9 mmol), and Toluene (200 mL). The reaction was heated to 100° C. and DPPA (4.8 mL, 22.2 mmol) was added dropwise. The reaction was stirred for 10 minutes, then cooled to ambient temperature, poured into dilute NaOH and extracted with EtOAc. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica (10 to 20% EtOAc in hexanes) to afford tert-butyl 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)pyridin-2-ylcarbamate (8.4 g, 72.5% yield).

Provenance & Evidence