Dimethylformamide → HCID 86699865, compound

Participants

Reaction Steps

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 114f (540 mg, 1.36 mmol), triethylamine (275 mg, 2.72 mmol) and anhydrous DMF (10 mL). Benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP, 782 mg, 1.77 mmol) was added, and the reaction was stirred at room temperature for 16 h. After this time, the reaction was diluted with water (20 mL), and the resulting suspension was filtered. The filter cake was dissolved in methylene chloride (40 mL), and the solution was washed with saturated aqueous sodium bicarbonate (10 mL), and water (10 mL), and dried over sodium sulfate. The drying agent was removed by filtration, and the solvent was evaporated under reduced pressure. The resulting residue was purified by flash chromatography to afford a 60% yield of 114g (305 mg) as a white solid: mp 55-56° C.; 1H NMR (500 MHz, CDCl3) δ 7.65 (d, 1H, J=8.0 Hz), 7.25 (m, 1H), 7.20 (d, 1H, J=8.0 Hz), 6.89 (s, 1H), 4.68 (s, 2H), 4.66 (s, 2H), 1.46 (s, 9H).

Provenance & Evidence