Triphenylphosphine → 4-(5-Methyl-pyridin-2-ylmethoxy)-1-{2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To 320 mg (0.84 mmol) 4-hydroxy-1-{2-[3-(2,2,2-trifluoro-acetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-ethyl}-1H-pyridin-2-one (preparation 21b) in 25 mL DCM is added 129 mg (1.05 mmol) (5-methyl-pyridin-2-yl)-methanol and 221 mg (0.84 mmol) triphenylphosphane. The reaction mixture is cooled to 0° C. and 174 μL (0.84 mmol) diisopropyl azodicarboxylate is added. The reaction mixture is stirred 16 h at RT and then additional 221 mg (0.84 mmol) triphenylphosphane and 174 μL (0.84 mmol) diisopropyl azodicarboxylate is added. The mixture is stirred 2 h at RT, the solvent is evaporated and to the residue water is added. The aqueous phase is extracted with DCM, dried over Na2SO4 and the solvent is evaporated. The residue is purified via reverse HPLC chromatography (Zorbax stable bond, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 5:95).

Provenance & Evidence