Orm-10103 → 2-[2-(3,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine

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Reaction Steps

2-[2-(3,5-Difluorophenyl)chroman-6-yloxy]-5-nitropyridine was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 340 mg of 2-(3,5-difluorophenyl)chroman-6-ol. The product was purified on preparative TLC-plate covered with silica gel using toluene-ethyl acetate as an eluant and then crystallised from 2-propanol. 1H NMR (400 MHz, d6-DMSO) δ:9.04 (d, 1H, J 2.9 Hz), 8.60 (dd, 1H, J 9.1, 2.9 Hz), 7.23-7.19 (m, 4H), 7.01-6.95 (m, 3H), 5.18 (dd, 1H, J 10.0, 2.1 Hz), 2.97 (ddd, 1H, J −16.9, 10.9, 5.7 Hz), 2.76 (ddd, 1H, J −16.9, 8.4, 4.7 Hz), 2.22 (m, 1H), 1.99 (m, 1H).

Provenance & Evidence