Sodium Azide → 5-(4-Chlorophenyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2-({1-[2-(trifluoromethyl)phenyl]-1H-1,2,3-triazol-4-yl}methyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

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Reaction Steps

20 mg (0.31 mmol) of sodium azide were initially charged in 1 ml of methanol, and 58 mg (0.31 mmol) of 2-(trifluoromethyl)phenylboronic acid and 6 mg (0.03 mmol) of copper(II) acetate monohydrate were added. The mixture was stirred at RT for 18 h. 0.9 ml of water, 30 mg (0.15 mmol) of L-ascorbic acid sodium salt and 117 mg (0.34 mmol) of the compound from Example 14A were then added to the mixture. The mixture was stirred at RT for a further 18 h. For work-up, the mixture was diluted with 10 ml of water and 10 ml of ethyl acetate, and 5 ml 0.1 N aqueous sodium hydroxide solution were added with stirring. After phase separation, the aqueous phase was extracted three more times with in each case 10 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1, then 1:2). This gave 117 mg (71% of theory) of the target compound.

Provenance & Evidence