Tetrabutylammonium Fluoride → 5-bromo-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium fluoride (1 M solution in tetrahydrofuran) (58.5 mL, 58.5 mmol) was added to a solution of 5-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine (16.5 g, 53 mmol) in tetrahydrofuran (15 mL) at 25° C. The mixture was stirred at 25° C. for 30 min and then extracted with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to afford 5-bromo-1H-pyrrolo[2,3-b]pyridine (7.4 g, 71%) as a light yellow solid: LC/MS m/e calcd for C7H6BrN [M+H]+ 198.04, observed 197.1, 199.1; 1H NMR (400 MHz, CDCl3) δ ppm 6.49 (m, 1H), 7.39 (m, 1H), 8.10 (s, 1H), 8.38 (s, 1H), 10.48 (br. s., 1H).

Provenance & Evidence