Sodium Carbonate → methyl 3-((1-(benzyloxycarbonylamino)-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl 5-(chloromethyl)-2,3-dihydro-1H-inden-1-ylcarbamate (2.10 g, 6.7 mmol), methyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5-(trifluoromethyl)benzoate (2.21 g, 7.0 mmol), trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) (269 mg, 0.3 mmol), and sodium carbonate (3.52 g, 33.2 mmol) in degassed THF (40 mL) and water (20 mL) was stirred at 80° C. After 3 h the reaction was cooled to rt and diluted with ethyl acetate (200 mL) and washed with brine (2×200 mL). The aqueous phases were extracted once more with ethyl acetate (1×100 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford a grey solid. The material was purified by silica flash column chromatography (100 g silica, EtOAc/heptane, from 0% to 25% of EtOAc) to afford the title compound as a white solid (2.8 g, 87%). MS (ESI): m/z [M+NH4]+ 501.2.

Provenance & Evidence