Trifluoroacetic acid → (3-Chloro-benzyl)-[5-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-1-methyl-1H-pyrazol-3-yl]-amine

Participants

Reaction Steps

To [5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-(5-fluoro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (147, 0.070 g, 0.13 mmol) in 4 mL of dichloromethane, triethylsilane (0.210 mL, 1.31 mmol) and trifluoroacetic acid (0.100 mL, 1.30 mmol) were added and the reaction stirred overnight at room temperature. The reaction was concentrated under vacuum, then ethyl acetate was added, then washed with 1M aqueous potassium carbonate, then brine. The organic layer was dried over sodium sulfate, filtered and the filtrate purified by silica gel flash column chromatography eluting with a gradient of 2-20% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum and the resulting solid washed with ethyl acetate in hexane to provide the desired compound.

Provenance & Evidence