反应详情

To a microwave tube with a magnetic stirring bar was charged CuI (382 mg, 2.0 mmol), Cs2CO3 (6.5 g, 20.0 mmol), 4-methyl-1H-imidazole (1.15 g, 14.0 mmol), 5-bromopyridin-2-amine (1.75 g, 10.0 mmol), and DMF (10 mL) under N2. The system was sealed and then evacuated twice and back filled with N2. The reaction mixture was stirred for 30 min at room temperature, and then heated at 120° C. for 48 h. The reaction mixture was then cooled to ambient temperature, diluted with 30 mL of ethyl acetate, washed with water. The combined organic layers were concentrated, and the resulting residue was purified by column chromatography on silica gel to provide 5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (134). 1H NMR (400 MHz, d6-DMSO) δ 8.09 (m, 1H), 7.85 (d, J=1.6 Hz, 1H), 7.56 (dd, J=2.8, 8.8 Hz, 1H), 7.22 (t, J=1.2 Hz, 1H), 6.51 (dd, J=0.8, 8.8 Hz, 1H), 6.15 (s, 2H), 2.14 (d, J=1.2 Hz, 3H). MS m/z 175.1 (M+1)+.

1. customThe system was sealed
2. customevacuated twice
3. additionback filled with N2
4. temperatureheated at 120° C. for 48 h
5. temperatureThe reaction mixture was then cooled to ambient temperature
6. additiondiluted with 30 mL of ethyl acetate
7. washwashed with water
8. concentrationThe combined organic layers were concentrated
9. customthe resulting residue was purified by column chromatography on silica gel