Trifluoroacetic acid → HCID 67201069, compound

Participants

Reaction Steps

In a round bottom flask, {5-[(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-6-fluoro-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (166, 1.15 g, 1.65 mmol) was combined with 50 mL of 1,2-dichloroethane, trifluoroacetic acid (0.635 mL, 8.24 mmol), and triethylsilane (1.32 mL, 8.24 mmol). The reaction was heated at reflux for 20 hours, then concentrated under vacuum. The residue was dissolved in 10 mL of trifluoroacetic acid and stirred at room temperature for 18 hours, then concentrated under vacuum and combined with aqueous sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with sodium bicarbonate, water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (167, 403 mg). MS (ESI) [M−H+]−=460.8 and 462.8.

Provenance & Evidence