Potassium Carbonate → 1-(3-Fluoro-4-pyridinylamino)-5-phenylmethoxy-1H-indole

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Reaction Conditions

Reaction Steps

To 250 ml 1-methyl-2-pyrrolidinone was added 5-phenylmethoxy-1H-indol-1-amine (27.3 g), and the mixture was heated to 80° C. Then, 4-chloro-3-fluoropyridine hydrochloride (22 g) was added, and the mixture was heated at 80° C. for two hours. After cooling, the mixture was poured into 1 liter of ice-water, stirred for five minutes, and adjusted to pH 9 with milled K2CO3. The product was extracted with ethyl acetate (3×). The organic layer was washed with water (2×) and dried (saturated NaCl, anhydrous MgSO4). After filtration, the filtrate was concentrated to give an oil, 46 g of which was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC. The desired fractions were combined and concentrated to give an oil, which solidified on cooling, 32.2 g, m.p. 140° C. A sample of this material was recrystallized from ether, m.p. 157°-159° C.

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