Potassium Fluoride → HCID 71212594, compound

Participants

Reaction Steps

To a mixture of 1-tert-butyl 2-ethyl 7-chloro-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate (88 mg, 0.17 mmol), 3-ethoxyphenylboronic acid (69 mg, 0.42 mmol), KF (38.7 mg, 0.67 mmol), and bis(tri-t-butylphosphine)palladium (0) (8.50 mg, 0.02 mmol) was added dioxane (3.5 mL) under a nitrogen atmosphere. The reaction was then heated to 100 C overnight. Another charge of 3-ethoxyphenylboronic acid (69 mg, 0.42 mmol), KF (38.7 mg, 0.67 mmol), and bis(tri-t-butylphosphine)palladium (0) (8.50 mg, 0.02 mmol) was then added and stirring was continued for 4 h. The crude reaction mixture was then concentrated in vacuo, and the crude material was purified on silica (gradient elution, 0-50% EtOAc/hexanes) to yield the title product (80 mg) as a mixture with Boc'd material 1-tert-butyl 2-ethyl 7-(3-ethoxyphenyl)-3-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[2,3-c]pyridine-1,2-dicarboxylate. HRMS (ESI) calc (M+H)+=515.1788. found 515.1772.

Provenance & Evidence