Reaction #67879

Reaction equation

Hydrochloric acid

3-Fluoro-isonicotinic acid

4-(trifluoromethylthio)aniline

LiHMDS

→

desired product

Yield 10.0%

3-(4-Trifluoromethylsulfanyl-phenylamino)-isonicotinic acid

Yield 10.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureto warm to room temperature over night
2. 2
   Otherthe volatiles were removed in vacuo
3. 3
   OtherThe crude material was purified by preparative HPLC

Procedure

3-Fluoro-isonicotinic acid (50 mg, 0.354 mmol) and 4-(trifluoromethylthio)aniline (68.5 mg, 0.354 mmol) was added to 2 ml dry THF and the mixture was cooled to −78° C. LiHMDS (1M in THF, 1.24 ml) was added and the mixture was allowed to warm to room temperature over night. Hydrochloric acid (1M in methanol, 5 ml) was added and the volatiles were removed in vacuo. The crude material was purified by preparative HPLC to give 11.4 mg (45 μmol; 10% yield) of pure desired product.

Source