Triphenylphosphine → HCID 68902396, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of aryl iodide (191) (100 mg, 0.19 mmol), pyridine-3-boronic acid 1,3-propanediol cyclic ester (61 mg, 0.38 mmol), palladium acetate (4 mg, 0.019 mmol) and triphenylphosphine (10 mg, 0.38 mmol) in tetrahydrofuran (10 mL) was added sodium bicarbonate (10 mL, saturated aqueous). The reaction mixture was heated to reflux (65° C.) for 4 h, cooled, filtered and partitioned between water (20 mL) and ethyl acetate (20 mL). The organic phase was separated and washed with brine (20 mL), dried (Na2SO4), filtered and the solvent removed under reduced pressure to afford the crude product as a yellow oil. Purification by silica gel chromatography (50% ethyl acetate/iso-hexane eluant) followed by preparative HPLC gave the title compound (194) as a colourless gum (7.7 mg, 8.5% yield).

Provenance & Evidence