2-Iodopyridin-3-ol → HCID 18396224, compound

Participants

Reaction Steps

A 3.14 g (14.4 mmol) sample of 2-iodo-3-hydroxypyridine (Lancaster Chem. Co.) was dissolved in 5 mL of DMF, and (Ph3P)2PdCl2 (0.34 g, 0.50 mmol), CuI (0.371 g, 1.98 mmol) and triethylanine (1.80 mL, 13.2 mmol) were added. The mixture was stirred under N2 at room temperature for 1 hour, then 2.15 g (11.0 mmol) of the compound from step 3a above, dissolved in 5 mL of DMF, was added carefully. The mixture was stirred at 60° C. for 16 hours, then cooled to room temperature. The reaction mixture was diluted with ether and filtered. The solution was washed with 10% NaOH, 50% brine, dried over MgSO4, and the solvent Awas removed. The residue was chromatographed on silica gel, eluting with 100:0 to 60:40 hexane:EtOAc to give 620 mg of title compound: 1H NMR (CDCl3, 300 MHz) δ 1.73 (s, 9H), 1.85-2.30 (m, 4H), 3.05-3.22 (m, 2H), 4.42 (m, 1H), 6.78 (s, 1H), 7.16 (dd, 1H), 7.68 (dd, 1H), 8.48 (dd, 1H); MS m/z: 289 (M+H)+.

Provenance & Evidence