1H-Pyrrolo(2,3-b)pyridine → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

NaH (4.90 g, 203.2 mmol) was added to a solution of 1H-pyrrolo[2,3-b]pyridine (20.0 g, 169.3 mmol) in dry DMF (200 mL) under N2 protection. The mixture was stirred at 0° C. for 1 hour. Then SEMCl (42.2 g, 253.95 mmol) was added to the reaction mixture, and the mixture was stirred at 0° C. for 4 hours. After concentrated in vacuo to remove DMF, ice cold NH4Cl (sat. aq.) was added and the mixture was extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4, filtered and the solvent was concentrated in vacuo under reduced pressure. The crude product was purified using column chromatography (petroleum ether:EtOAc=10:1) to provide the product of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (31.2 g, yield: 74%). 1H-NMR (CDCl3, 400 MHz) δ 8.33 (dd, J=4.8 Hz, 1.6 Hz, 1H), 7.91 (dd, J=7.6 Hz, 1.6 Hz, 1H), 7.34 (d, J=3.6 Hz, 1H), 7.08 (dd, J=7.6 Hz, 4.8 Hz, 1H), 6.51 (d, J=3.6 Hz, 1H), 5.68 (s, 2H), 3.53 (t, J=8.4 Hz, 2H), 0.90 (t, J=8.4 Hz, 2H), −0.08 (s, 9H). MS (M+H)+: 249.

Provenance & Evidence