反应详情

温度

0 °C

Ethyl 7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (Reference Example 3) (11.2 g, 29.0 mmol) was dissolved in tetrahydrofuran (150 mL) while stirring under N2 at 0° C. Lithium aluminum hydride (1.65 g, 43.4 mmol) was added in three portions, while monitoring the gas evolution and temperature. After the final addition, the reaction mixture was stirred at room temperature for 3 h and then heated at 60° C. for 3 h. The reaction mixture was cooled to 0° C. and quenched with freshly prepared hydrated sodium sulfate. The solid was removed by filtration and washed thoroughly with tetrahydrofuran. Concentration of the filtrate provided [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol (9.8 g, 99%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ4.63 (2H, s), 4.78 (4H, s), 6.26 (1H, s), 6.98 (1H, d, J=5.54 Hz), 7.27-7.38 (10H, m), 7.84 (1H, d, J=5.7 Hz), 8.27 (1H, br s).

1. additionAfter the final addition
2. stirringthe reaction mixture was stirred at room temperature for 3 h
3. temperatureheated at 60° C. for 3 h
4. temperatureThe reaction mixture was cooled to 0° C.
5. customquenched with freshly prepared hydrated sodium sulfate
6. customThe solid was removed by filtration
7. washwashed thoroughly with tetrahydrofuran