Water → 1H-Pyrrolo[2,3-b]pyridine, 6-fluoro-1-methyl-

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Reaction Steps

To a solution of 6-fluoro-1H-pyrrolo[2,3-b]pyridine (250 g, 1.84 mol) in dimethylformamide (2.50 L) is added potassium carbonate (507.6 g; 3.67 mol), followed by methyl iodide (171.6 mL, 2.75 mol). The reaction is stirred at room temperature overnight. The reaction mixture is poured into water (3000 mL) and extracted with Et2O (3×1500 mL). The organic extracts are combined and washed with water (4×1000 mL), then brine, and dried over Na2SO4. The solvent is evaporated to give a light brown oil which, on standing, gives clear colorless crystals, with a little mobile liquid on top of the crystals. The liquid is decanted off and discarded to leave the product as a crystalline solid (257.3 g, 1.71 moles). 1H-NMR (400 MHz, CDCl3): δ 7.93 (t, 1H), 7.11 (d, 1H), 6.69 (d, 1H), 6.46 (d, 1H), 3.83 (s, 3H).

Provenance & Evidence