Ammonium formate → (S)-2-[5-(3-Amino-4-ethyl-6-methoxy-5-trifluoromethyl-pyridin-2-yl)-[1,3,4]oxadiazol-2-yl]-1,1,1-trifluoro-propan-2-ol

Participants

Reaction Steps

To a stirring solution of (S)-2-(5-(3-amino-6-methoxy-5-(trifluoromethyl)-4-vinylpyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol (step 1)(153 mg, 0.384 mmol) in EtOH (10 ml) was added palladium hydroxide on carbon (43.2 mg, 0.307 mmol) followed by ammonium formate (969 mg, 15.37 mmol). The reaction mixture was heated at relux for 30 minutes. The mixture was filtered through Celite® and diluted with EtOAc. The filtrate and washed with sat.NaHCO3, water, brine and dried over MgSO4. Isolute Si-TMT (2,4,6-trimercaptotriazine silica, palladium scavenger) was added the mixture was stirred for 30 mins and filtered. The solvent was removed in vacuo and purification of the crude product by chromatography on silica eluting with 0-30% EtOAc in iso-hexane afforded the title compound;

Provenance & Evidence