Reaction #474636

Reaction equation

K2CO3

potassium bis(trimethylsilyl)amide

3-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H[1,2,4]triazol-3-yl]-phenol

4-chloro-2-pyridine-carboxamide

→

TFA

4-{3-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H-[1,2,4]triazol-3-yl]-phenoxy}-pyridine-2-carboxylic acid methylamide trifluoroacetic acid salt

Solvents

MeOH

DMF

Conditions

Workup

1. 1
   OtherThen the vial was capped
2. 2
   Othermicrowaved at 250° C. for 20 min
3. 3
   Filtrationfiltered through 0.22 um syringe
4. 4
   Filtrationfilter
5. 5
   Otherpurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA

Procedure

3-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H[1,2,4]triazol-3-yl]-phenol (100 mg, 0.282 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (140.6 mg, 0.705 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 4-chloro-2-pyridine-carboxamide (52.9 mg, 0.31 mmol) was added, followed by anhydrous K2CO3 (19.5 mg, 0.141 mmol). Then the vial was capped and microwaved at 250° C. for 20 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. The product was isolated as a TFA salt (25.0 rug of white solid).

Source