Dimethylformamide → [2-Bromo-5-(4-chlorophenyl)pyridin-3-yl]dimethylamine

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Reaction Steps

169 mg (3.88 mmol) of sodium hydride (55% suspension) was added batchwise under a nitrogen atmosphere to a solution of 0.50 g (1.76 mmol) of 2-bromo-5-(4-chlorophenyl)pyridin-3-ylamine (Example 16.1c) in 10 mL of DMF and the mixture was stirred for 15 minutes at RT. A solution of 0.22 mL (3.53 mmol) of methyl iodide in 0.5 mL of DMF was added and the mixture was stirred for 16 hours at RT. The reaction mixture was diluted with semisaturated aqueous sodium bicarbonate solution and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with water, dried over magnesium sulfate, and evaporated down in vacuo. Yield: 0.47 g (85% of theoretical); C13H12BrClN2 (M=311.605); calc.: molpeak (M+H)+: 311/313/315 (BrCl); found: molpeak(M+H)+:311/313/315 (BrCl).

Provenance & Evidence