Sodium Carbonate → HCID 178517589, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-3-iodopyridin-2-ol (5 g, 16.7 mmol), (4-fluoro-1H-indol-2-yl)boronic acid (4.48 g, 25.0 mmol), sodium carbonate (3.53 g, 33.4 mmol) and Pd(dppf)Cl2 (200 mg) in 1,4-dioxane (50 mL) was stirred at 100° C. for 16 hours under nitrogen atmosphere. The mixture was filtered through celite and concentrated, and the residue was diluted with water and EA. After extracted with EA, the combined organic phase was washed with brine, dried over sodium sulfate and concentrated to afford crude 5-bromo-3-(4-fluoro-1H-indol-2-yl)pyridin-2-ol (3.5 g) through the column chromatography (DCM:EA=5:1). Finally the pure 5-bromo-3-(4-fluoro-1H-indol-2-yl)pyridin-2-ol (2.7 g, yield: 52%) was obtained by recrystallized from DCM:MeOH (10:1). 1H-NMR (DMSO-d6, 400 MHz) δ 12.36 (br s, 1H), 11.79 (s, 1H), 8.25 (s, 1H), 7.70 (s, 1H), 7.39 (s, 1H), 7.30 (d, J=8.00 Hz, 1H), 7.04˜7.07 (m, 1H), 6.74˜6.78 (m, 1H). MS (M+H)+: 307/309.

Provenance & Evidence