1,4-Dioxane → Benzyl {2-[({4-[(3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-vinylquinolin-3-yl}carbamate

Participants

Reaction Conditions

Reaction Steps

A pressure tube charged with benzyl {7-bromo-2-[({4-[(3R,4S,5S)-3-[(tert-butoxycarbonyl)amino]-5-methyl-4-(1H-1,2,3-triazol-1-yl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]quinolin-3-yl}carbamate (15 mg, 0.020 mmol), K3PO4 (8.4 mg, 0.04 mmol), 1,4-dioxane (0.26 mL), water (0.042 mL) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (5.5 mg, 0.036 mmol). The reaction mixture was purged with nitrogen for 5 min., then dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (1.6 mg, 0.002 mmol) was added. The pressure tube was sealed and the reaction mixture was heated at 90° C. for 30 min. then allowed to cool. The crude mixture was filtered and purified by preparative LCMS (pH=10 method; XBridge™ preparative C18 5 μm OBD™ column, 30×10 mm, 60 mL/min., eluting with a gradient of MeCN and water with 0.1% NH4OH) to give the sub-title compound as a light yellow powder (5.2 mg, 37%). LCMS calc. for C38H42N9O5 (M+H)+: m/z=704.3. Found: 704.3.

Provenance & Evidence