Sodium Iodide → HCID 67261265, compound

Participants

Reaction Steps

A mixture of (2,4-difluoro-phenyl)-(6-methoxy-pyridin-3-yl)methanol 2 (2.28 g, 9.1 mmol), sodium iodide (5.45 g, 36.4 mmol), triethylsilane (2.2 ml, 13.6 mmol) in anhydrous acetonitrile (21 ml) and was stirred at room temperature. TFA (1.1 ml, 14.3 mmol) was added at a rate that maintained the temperature below 30° C.; TMSCl (5.8 ml, 45.5 mmol) was added, and the batch was heated at 70° C. for 3 h. Upon cooling to 55° C., a 0.8 M Na2SO3 (11.4 ml) was added, and the reaction mixture was concentrated in vacuo to 20 ml. A solution of 0.15 M Na2SO3 (11.4 ml) was added, the mixture was stirred at room temperature overnight. A solution of 1.4 M K2CO3 (13.6 ml) was added and cooled to 0° C. The crude product was extracted with ethyl acetate (60 ml) and washed with 0.15 M Na2SO3 (20 ml) and water (60 ml) and dried over anhydrous sodium sulfate. The mixture was distilled, and the residue was purified by flash column chromatography on silica gel (chloroform:methanol, 90:10). Yield 1.89 g (94%). 1H NMR (CDCl3, 500 MHz): δ 13.35 (s, 1H), 7.36-6.79 (m, 7H), 6.53 (d, 1H, J=9.2 Hz), 3.71 (s, 2H). 13C NMR (CDCl3, 125 MHz): δ 164.7, 162.4, 160.4, 143.2, 132.7, 131.2, 122.3, 120.3, 118.4, 111.4, 104.1, 30.3.

Provenance & Evidence