6-Chloro-2-iodo-3-hydroxypyridine → HCID 86728233, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-chloro-2-iodopyridin-3-ol (8.39 g, 32.85 mmol), (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)boronic acid (8.00 g, 27.38 mmol) and K3PO4.3H2O (22 mg, 82.13 mmol) in 1,4-dioxane (120 mL), Pd(dppf)Cl2 (50 mg) was added under N2 protection. After stirred overnight at 80° C., the reaction mixture was concentrated in vacuo, suspended in water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using column chromatography (petroleum ether:EtOAc=5:1) to provide the product of 6-chloro-2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)pyridin-3-ol (3.01 g, yield: 29%). 1H-NMR (CDCl3, 400 MHz) δ 8.40 (dd, J=4.8 Hz, 1.6 Hz, 1H), 7.96 (dd, J=8.0 Hz, 1.6 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.17 (dd, J=8.0 Hz, 4.8 Hz, 1H), 6.82 (s, 1H), 5.85 (s, 2H), 3.65 (t, J=8.4 Hz, 2H), 0.89 (t, J=8.4 Hz, 2H), −0.08 (s, 9H). MS (M+H)+: 376/378.

Provenance & Evidence