Water → HCID 22031800, compound

Participants

Reaction Conditions

Reaction Steps

2 g 6-bromo-3-(2-pyridyl)imidazo[1,2-a]pyridine (compound in Production Example 63) and 5 g mixture of methyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate and ethyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-1H-3-pyrazolyl]benzoate were reacted in the same manner as in Example 10, whereby 4.54 g mixture of methyl 4-[4-(3-pyridin-2-ylimidazo[1,2-a]pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]-benzoate and ethyl 4-[4-(3-pyridin-2-ylimidazo[1,2-a]-pyridin-6-yl)-1-trityl-1H-pyrazol-3-yl]benzoate was obtained as a pale yellow amorphous. 638 mg of this ester mixture was added to 10 mL suspension of 50 mg lithium aluminum hydride in tetrahydrofuran, and the mixture was stirred at 50° C. for 2 hours. The reaction solution was cooled on iced water, then 220 mg sodium fluoride and 80 μL water were added thereto, and the reaction solution was returned to room temperature and stirred for 40 minutes. Insolubles were filtered off, and the filtrate was evaporated. The residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 298 mg of the title compound as white crystals.

Provenance & Evidence