Sodium Carbonate → 5-(2-Amino-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-N-tert-butylpyridine-3-sulfonamide

Participants

Reaction Conditions

Reaction Steps

5-bromo-N-tert-butylpyridine-3-sulfonamide (375 mg, 0.986 mmol), bis(pinacolato) diboron (276 mg, 1.085 mmol), potassium acetate (290 mg, 2.96 mmol), [1,1′bis(diphenylphosphino)ferrocene]dichloro-palladium (II) complex with CH2Cl2 (40 mg, 0.049 mmol) and dioxane (3 ml) were heated to 120° C. for 60 minutes in the microwave. After this time aryl bromide (A) (147 mg, 0.69 mmol), Na2CO3 (2M aqueous solution, 2 mL), EtOH (0.4 ml) and a further portion of [1,1′bis(diphenylphosphino)ferrocene]dichloro-palladium (II) complex with CH2Cl2 was added and reaction mixture heated further for 60 minutes at 120° C. in the microwave. After this time the solvents were removed in vacuo and the brown residue redissolved in 2M HCl (30 mL), the aqueous phase was washed with ethyl acetate (3×20 mL) and then neutralized with concentrated NaOH to pH 7.0. The aqueous phase was then extracted with ethyl acetate (3×20 mL), the organic extracts were combined, dried over sodium sulfate, filtered and the solvent removed in vacuo to afford the desired product as a brown solid (441 mg, 54%).

Provenance & Evidence