Triphenylphosphine → (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-((6-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)pyridin-2-yloxy)methyl)pyrrolidine-1-carboxylate

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To a suspension of N-(3-ethyl-1-((6-hydroxypyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (26 mg, 0.0630 mmol; prepared as in Example 17, Step A) in THF (5 mL) was added (2S,3S)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (62.7 mg, 0.189 mmol), triphenylphosphine (54.6 mg, 0.208 mmol) and diethyl azodicarboxylate (81.9 μL, 0.208 mmol). The suspension became a clear solution, which was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure and silica gel chromatography (DCM/MeOH 10:1) provided the product mixed with triphenyl phosphine oxide (65.6 mg).

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