Imidazole → Pyridine, 2-(1,1-difluoro-2-iodoethyl)-5-methyl-

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Reaction Conditions

Reaction Steps

2,2-Difluoro-2-(5-methyl-pyridin-2-yl)-ethanol (8.5 g, 0.05 mol), as prepared in the previous step, was dissolved into toluene:CH3CN (98 mL, 2:1) and cooled to 0° C. To this solution was added PPh3 (19.3 g, 0.074 mol, 1.5×), imidazole (6.7 g, 0.098 mol, 2×) and I2 (18.7 g, 0.074 mol, 1.5×). The reaction was heated to 90° C., then was cooled to RT and concentrated in vacuo to afford a thick amber oil. Purification via flash chromatography (CH2Cl2) afforded the product as a clear oil (4.6 g, 0.016 mol, 33% yield). 1H NMR (300 Hz, CDCl3) δ 8.48 (s, 1H), 7.61 (m, 1H), 3.92 (t, J=14.7 Hz), 2.41 (s, 3H); LC/MS (m/z) [M+1]+ 284.1 (calculated for C8H9F2IN, 284.07).

Provenance & Evidence