Ethyl Acetate → HCID 86647437, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 205 mg (1.027 mmol) of methyl 2-chloro-6-formylisonicotinate, 183 mg (1.64 mmol) of 2-furanboronic acid, and 316 mg (2.98 mmol) of Na2CO3 in 2 mL of H2O and 4 mL of THF was added 263 mg (0.227 mmol) of Pd(PPh3)4. The mixture was stirred at 55° C. for 14 h, and EtOAc and H2O were added. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided methyl 2-formyl-6-(furan-2-yl)isonicotinate as a yellow solid (101 mg) in 43% yield. The desired 6-(furan-2-yl)-4-(methoxycarbonyl)picolinic acid was synthesized from the aldehyde (methyl 2-formyl-6-(furan-2-yl)isonicotinate) following the general procedures as described herein.

Provenance & Evidence