4-Chloro-3-(trifluoromethyl)aniline → 5-(2-Amino-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (4-chloro-3-trifluoromethyl-phenyl)-amide

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Reaction Steps

90 mg (0.30 mMol) triphosgene are dissolved in 5 ml ice-cooled CH2Cl2. Then a solution of 148 mg (0.76 mMol) 5-amino-2-chloro-benzotrifluoride and 0.3 ml (1.72 mMol) EtN(iPr)2 in 5 ml CH2Cl2 is added during 15 min. After stirring the reaction mixture for further 15 min, a solution of 200 mg (0.88 mMol) 5-(2-amino-pyrimidin-4-yloxy)-2,3-dihydro-1H-indole (Step 26.2) and 0.3 ml (1.72 mMol) EtN(iPr)2 in 5 ml THF is added. After 16 h at rt, the mixture is diluted with 10% NaHCO3 solution and CH2Cl2, the aqueous phase separated off and extracted twice with CH2Cl2. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; 1% MeOH in CHCl3) gives the title compound: MS: [M+1]+=450; HPLC: EtRet=3.7.

Provenance & Evidence