Trifluoroacetic acid → HCID 57969693, compound

Participants

Reaction Steps

N,N,2-trimethyl-2-(3-(1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)butan-1-amine (89.3 mg, 0.1621 mmol) was dissolved in dry DCM (2 mL) and cooled in an ice-bath. Triethylsilane (75.39 mg, 103.6 μL, 0.6484 mmol) was added followed by TFA (2 mL). The resultant mixture was stirred at 0° C. for 85 minutes and then concentrated under vacuo. The residue was partitioned between EtOAc and 1:1 c.HCl/water. The organic layer was extracted further with 1:1 c.HCl/water (3×20 mL) and the combined aqueous material was cooled in an ice-bath and carefully basified with 5M NaOH. The basic aqueous mixture was extracted with EtOAc (3×20 mL) and the combined organics were washed with brine (3×10 mL), dried over Na2SO4, filtered and concentrated under vacuo to give a yellow gum. This was purified by column chromatography (10% MeOH in DCM, ˜75 mL silica) to give a colourless gum which was triturated with pentane to give a white powder (12.3 mg, 24% Yield).

Provenance & Evidence