Acetic Acid → 3-bromo-N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine

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Reaction Steps

Sodium triacetoxyborohydride (159 mg, 0.750 mmol) and then acetic acid (29 μl, 0.507 mmol) were added to a suspension of 3-bromo-1H-indazol-5-amine (106 mg, 0.500 mmol) and 8-propyl-8-azabicyclo[3.2.1]octan-3-one (100 mg, 0.598 mmol) in dichloroethane (3 ml), and the resulting mixture was stirred at room temperature for 1 day. Aqueous ammonia was added thereto, followed by extraction with ethyl acetate. The extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel column chromatography (chloroform/methanol/triethylamine=100/10/5) and a preparative thin-layer chromatography (200×200×0.5 mm, eluent: chloroform/methanol/triethylamine=100/5/5) to obtain 3-bromo-N-(8-propyl-8-azabicyclo[3.2.1]oct-3-yl)-1H-indazol-5-amine (2 mg, 1%).

Provenance & Evidence