Sodium hydride → (3R,4R)-tert-butyl 4-(4-((3-ethyl-4-(imidazo[1,2-a]pyridine-3-carboxamido)-1H-indazol-1-yl)methyl)-1H-pyrazol-1-yl)-3-fluoropiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To N-(1-((1H-pyrazol-4-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (40 mg, 0.10 mmol; prepared according to Example 21, Step A) in DMA (5 mL) was added sodium hydride (7.5 mg, 0.31 mmol) and a mixture (approximately 9:1) of (3R,4S)-tert-butyl 3-fluoro-4-(methylsulfonyloxy)piperidine-1-carboxylate (prepared as in WO 2008/124323) and tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (62 mg). The reaction mixture was heated to 80° C. and stirred for 3 hours. The mixture was concentrated under reduced pressure and silica gel chromatography (DCM/MeOH 10:1) gave the product (21 mg).

Provenance & Evidence