3-(Trifluoromethyl)aniline → HCID 24763124, compound

Participants

Reaction Conditions

Reaction Steps

In a dried vessel, 66 mg (0.41 mMol) 3-trifluoromethyl-aniline are dissolved in 7 ml degassed toluene and cooled to 10° C. Then 650 μl Me3Al (2 M in toluene; 1.3 mMol) are added via syringe. After 45 min at rt, a solution of 100 mg (0.317 mMol) 6-(2-amino-pyrimidin-4-yloxy)-benzo[b]thiophene-3-carboxylic acid ethyl ester (Step 12.5) in 2.5 ml THF is added and the reaction mixture is stirred for 40 min in an oil bath of 110° C. The solution is cooled in an ice-bath and hydrolyzed with 15 ml of a sat. NH4Cl. After 10 min stirring, the mixture is filtered through Celite, the solid washed extensively with EtOAc and water, the aq. phase separated from the filtrate and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; EtOAc/hexane 9:1) and crystallization from CH2Cl2/hexane gives the title compound: MS: [M+1]+=431; TLC(EtOAc/hexane 9:1): Rf=0.24.

Provenance & Evidence