Dimethylformamide → HCID 123846402, compound

Participants

Reaction Conditions

Reaction Steps

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (700 mg, 3.61 mmol), 2,2-dimethyl-4-[(methylsulfonyl)oxy]cyclohexanecarboxylate (1.50 g, 3.97 mmol), and cesium carbonate (1.29 g, 3.97 mmol) were added to an oven-dried flask. DMF (12 mL) was added and the mixture was stirred at 90° C. for 22 hours. The mixture was cooled to room temperature, diluted with diethyl ether, washed with water (3×50 mL), and then brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (10 to 80% EtOAc/hexanes) to afford racemic methyl 2,2-dimethyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]cyclohexanecarboxylate. 1H NMR (500 MHz, DMSO-d6) δ 7.91 (s, 1H), 7.54 (s, 1H), 4.10 (q, J=7.3 Hz, 1H), 3.54 (s, 3H), 2.20-1.98 (m, 1H), 1.83-1.65 (m, 2H), 1.64-1.49 (m, 2H), 1.43-1.38 (m, 1H), 1.34-1.31 (m, 1H), 1.22 (s, 12H), 0.90 (s, 6H).

Provenance & Evidence