3-(Trifluoromethyl)aniline → HCID 86626629, compound

Participants

Reaction Conditions

Reaction Steps

10.5 μl (0.084 mMol) 3-Trifluoromethyl aniline are dissolved in 2 ml toluene and cooled to 5° C. 126 μl Me3Al (2 M solution in toluene; 0.25 mMol) are added slowly via a syringe followed by a solution of 27 mg (0.084 mMol) 6-(2-amino-6-chloro-pyrimidin-4-yloxy)-pyrazolo[1,5-a]pyridine-3-carboxylic acid methyl ester in 1 ml THF. The reaction is stirred at rt for 1 h and then heated to 110° C. for 30 min. The reaction is submitted to aq. workup with EtOAc/H2O. The organic layers are combined, dried and concentrated to give the crude product which is further purified by flash chromatography (SiO2, 4 g column, CH2Cl2/MeOH; gradient 0-10% MeOH) to give the title compound as a white solid: m.p.: 219-221° C.; MS: [M+1]+=449.

Provenance & Evidence