Potassium Fluoride → 6-Bromo-9H-pyrrolo[2,3-b:5,4-c′]dipyridine

Participants

Reaction Steps

A solution of 6′-bromo-2-fluoro-[3,4′]bipyridinyl-3′-ylamine (7.22 g, 26.9 mmol) in THF (75 mL) was added dropwise over 10 minutes to sodium bis-(trimethylsilyl)amide (1N solution in THF, 54 mL, 53.9 mmol). The reaction mixture was left to stir for 2.5 h then 1N aqueous potassium fluoride solution (7 mL) was added and the solvent evaporated in vacuo. The residue was diluted with water (100 mL) and the resultant solid was collected by filtration, washed with water (20 mL) and diethyl ether:pentane (1:1, 20 mL) and left to air dry. The resultant solid was triturated with methanol (50 mL), collected by filtration, washed with methanol (10 mL) and diethyl ether (20 mL) and pentane (20 mL) and left to air dry to afford the title compound as a brown solid (5.0 g, 75%). NMR (DMSO-D6, 300 MHz): 8.73-8.69 (m, 2H), 8.63 (dd, J=4.8, 1.7 Hz, 1H), 8.48 (dd, J=1.0 Hz, 1H), 7.33 (dd, J=7.8, 4.8 Hz, 1H). LCMS (Method B): RT=2.43 min, M+H+=248/250.

Provenance & Evidence