2-Fluoro-4-(tributylstannyl)pyridine → 4-(2-Fluoropyridin-4-yl)-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid potassium salt

Participants

Reaction Conditions

Reaction Steps

Methyl 4-chloro-1-{2-[4-(trifluoromethoxy)phenoxy]ethyl}-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (50 mg, 0.121 mmole), 2-fluoro-4-(tributylstannyl)pyridine (61 mg, 0.158 mmole), and bis(tri-t-butylphosphine)palladium(0) (6 mg, 0.012 mmole) were combined in a screw cap vial. To this was added 1,4-dioxane (0.5 mL). N2 was bubbled through the mixture for 10 seconds. The vial was capped then heated to 100° C. After stirring overnight the mixture was cooled to RT. Excess QuadraPure was added and stirring continued at RT. After stirring 6 hr the mixture was filtered washing with EtOAc and concentrated. The residue was taken up in 1 mL THF. To this was added KOTMS (47 mg, 0.366 mmole) at RT. After 3 hr the mixture was concentrated. The residue was taken up in Et2O. The resulting off-white solid (53 mg, 88%) was collected by filtration washing with Et2O and dried in vacuo. 1H NMR (400 MHz, DMSO): δ 8.39 (d, J=5.1 Hz, 1 H); 8.35 (d, J=5.9 Hz, 1 H); 7.95 (d, J=5.1 Hz, 1 H); 7.63 (d, J=6.3 Hz, 2 II); 7.21 (d, J=8.4 Hz, 2 H); 7.04 (s, 1 H); 6.95 (d, J=8.8 Hz, 2 H); 5.12-5.05 (m, 2 H); 4.39-4.33 (m, 2 H).

Provenance & Evidence