Dimethylformamide → 5-Cyclopentenyl-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

The mixture of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid (Example 9 d, 1.0 g, 4 mmol), 2-cyclopentenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAN 287944-10-9, 0.86 g, 4 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 150 mg 0.18 mmol) and aqueous sodium carbonate solution (2N, 16 mL) was added to DMF (10 ml). The mixture was heated to 100° C. overnight; then the solution was diluted with water (15 mL), extracted with ethyl acetate (30 mL), the water layer was adjusted to pH=3.0 by hydrochloric acid (3N) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water (2×100 mL) and brine (80 mL) and evaporated to dryness. The residue was purified by column chromatography (silica gel, 8 g, eluting with 15% ethyl acetate in petroleum ether) to obtain the product (0.85 g, 89%) as a white solid; MS (LC/MS): 260.1 [M+H]+.

Provenance & Evidence