Triethylamine → 5-(6-Hydroxymethyl-pyrimidin-4-yloxy)-2,3-dihydro-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide

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Reaction Steps

To an ice-cooled solution of 400 mg (0.9 mMol) 6-[1-(3-trifluoromethyl-phenylcarbamoyl)-2,3-dihydro-1H-indol-5-yloxy]-pyrimidine-4-carboxylic acid (Expl. 73) in 12 ml THF are added 137 μl (0.99 mMol) Et3N and 130 μl (0.99 mMol) iso-butyl-chloroformate. After 1 h the resulting suspension is added dropwise to 75 mg (1.98 mMol) NaBH4 in 10 ml of water. After 30 min the mixture is diluted with EtOAc and 1 M HCl, the aqueous layer separeted off and extracted twice with EtOAc. The organic phases are washed with 1 M NaOH, water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 1:1→1:9) gives the title compound: MS: [M+1]+=431; HPLC: AtRet=13.6.

Provenance & Evidence