Tetrabutylammonium Fluoride → 4-Fluoro-3-(1-methyl-1H-pyrazolo[3,4-c]pyridin-4-ylethynyl)-phenylamine

Participants

Reaction Conditions

Reaction Steps

In an adaption of GP 3c, 1000 mg of 4-bromo-1-methyl-1H-pyrazolo[3,4-c]pyridine (Intermediate 2.1, 4.7 mmol, 1 eq), 1590 mg 4-fluoro-3-trimethylsilanylethynyl-phenylamine (7.69 mmol, 1.63 eq.), 165 mg dichlorobis(triphenylphosphine)palladium (II) (PdCl2(PPh3)2) (0.24 mmol, 5 mol %) and 179 mg copper (I) iodide (0.94 mmol, 0.2 eq.) were dissolved in 8 mL THF (0.2 M) and treated with 16.5 mL tetra-n-butylammonium fluoride solution (1.0 M in THF, 16.5 mmol, 3.5 eq.). The resulting mixture was heated to 80° C. in a Biotage Initiator microwave oven for 30 min. Extractive work-up delivered the crude product which was used without further purification.

Provenance & Evidence