Water → 3-(4,5,2'-Trimethoxybiphenyl-2-ylmethylene)-1,3-dihydroindol-2-one

Tetrakis(triphenylphosphine)palladium(0) (0.02 g, 0.02 mmol) was added to a solution of 3-(3-bromo-4,5-dimethoxybenzylidene)-1,3-dihydroindol-2-one (0.20 g, 0.56 mmol) in toluene (1 ml) and ethanol (1 ml), followed by addition of 2M aqueous sodium carbonate (1.1 ml, 2.2 mmol). To this mixture was added 2-methoxyphenylboronic acid (0.09 g, 0.62 mmol), and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction mixture was added to water (50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml). The organic layer was dried over magnesium sulfate and concentrated. Chromatography (silica, 30-40% ethyl acetate/hexanes) afforded 0.14 g (64%) of 3-(4,5,2′-trimethoxy-biphenyl-2-ylmethylene)-1,3-dihydroindol-2-one as an orange solid.

1. extractionextracted with ethyl acetate (2×100 ml)
2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
3. dry with materialThe organic layer was dried over magnesium sulfate
4. concentrationconcentrated

ORD record

ord-23766819bdb742cc8acaacd93b4c925c

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06855730B2