Aluminium lithium hydride → [7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridin-2-yl]methanol

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence