1-Methyl-2-(tributylstannyl)-1H-imidazole → N-((1S)-1-((1R)-2-(((4'S)-6'-(2,2-dimethylpropyl)-8'-(1-methyl-1H-imidazol-2-yl)-3',4'-dihydrospiro[cyclobutane-1,2'-pyrano[2,3-c]pyridin]-4'-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-((1S)-1-((1R)-2-(((4′S)-8′-chloro-6′-(2,2-dimethylpropyl)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-c]pyridin]-4′-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)-2-methoxyacetamide (225 mg, 469 μmol) and tetrakis(triphenylphosphine)palladium (108 mg, 93.7 μmol) in THF (3.0 mL) is added to a vial with 1-methyl-2-(tributylstannyl)-1H-imidazole (217 mg, 586 μmol). The reaction was heated in the microwave at 160° C. for 20 min. The residue was diluted with H2O (10 mL) and extracted with CH2Cl2 (3×10 ml). The organic layers were dried (MgSO4), concentrated and purified by reverse phase HPLC to give the title compound as a white amorphous solid. MS m/z=526.3 [M+H]+.

Provenance & Evidence