Isopropanol → 3-Bromo-5-(propan-2-yloxy)pyridine

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Reaction Steps

To NMP (15 eq, 313 mmol, 30.4 ml), NaOtBu (1.5 eq, 31.3 mmol, 3.01 g) is added portion-wise. The mixture is stirred for 1 h at r.t., then 2-propanol (15 eq, 313 mmol, 24 ml) is added over a period of 15 min, followed by the addition of 3,5-dibromopyridine (Sigma-Aldrich, St. Louis, USA) (1 eq, 20.9 mmol, 5.0 g). The resulting mixture is heated at 75° C. for 2 h. After cooling down to r.t., toluene (30 ml) is added and the mixture is washed with water, dried over MgSO4, filtered, and concentrated. Purification of the crude product using column chromatography (hexane/EtOAc) yields the title compound; [M+H]+=217.

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