Cesium carbonate → HCID 67088891, compound

Participants

Reaction Steps

5-Nitro-1-tosyl-1H-pyrazolo[3,4-b]pyridin-3-ol (0.05 g, 0.150 mmol) was dissolved in DMF (1.5 mL). Cesium carbonate (0.146 g, 0.450 mmole) was added, and then 3-(iodomethyl)oxetane (0.030 g, 0.150 mmol; prepared according to US 2008/0021032) was added to the mixture. The mixture was stirred at room temperature for 16 hours. The mixture was then diluted with water and extracted with EtOAc (2×50 mL), and the extracts were washed with brine (1×), dried over sodium sulfate and concentrated under reduced pressure. Preparative TLC (0.5 mm plate, 1:1 ethyl acetate/hexanes) afforded 5-nitro-3-(oxetan-3-ylmethoxy)-1-tosyl-1H-pyrazolo[3,4-b]pyridine (15 mg, 19%) as a solid. 1H NMR (400 MHz, CDCl3) δ 9.54-9.52 (m, 1H), 8.83-8.81 (m, 1H), 8.05-7.99 (m, 2H), 7.34-7.28 (m, 2H), 4.93-4.86 (m, 2H), 4.78-4.72 (m, 2H), 4.62-4.55 (m, 2H), 3.57-3.48 (m, 1H), 2.40 (s, 3H).

Provenance & Evidence