Dichloromethane → HCID 86613794, compound

Participants

Reaction Conditions

Reaction Steps

Add 1,1′-bis(diphenylphosphino)(II) chloride, complex with dichloromethane (9 mg, 0.012 mmol) to a suspension of (+/−)-cis-4-[acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-2-ethyl-6-bromo-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (50 mg, 0.08 mmol), methyl boronic acid (15 mg, 0.24 mmol) and cesium fluoride (40 mg, 0.28 mmol) in dry dioxane (1.5 mL) and heat the mixture at 80° C. in a sealed tube for 15 h. Cool the reaction mixture to room temperature, add water and extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter and remove the solvent under reduced pressure. Chromatograph the residue over a silica gel cartridge, eluting with hexanes/ethyl acetate to provide the title compound (37 mg, 84%). MS (ES+): 546 (M+H).

Provenance & Evidence