Potassium Carbonate → Ethyl 3-(4-sulfamoylphenyl)furan-2-carboxylate

Temperature

100 °C

(4-sulfamoylphenyl) boronic acid (1.76. gm, 8.77 mmol) and Potassium carbonate (2.52 gm, 18.26 mmol) were added to a stirred suspension of ethyl 3-bromofuran-2-carboxylate (Prepared according to the procedure reported in the literature EP1489077A1, 2004, 1.6 gm, 7.30 mmol) in a mixture of 80 ml of ethanol and 20 ml of toluene (80 ml:20 ml) under nitrogen atmosphere at room temperature (25° C.) in a tube. A nitrogen gas was purged to the suspension for 15 minute at room temperature (about 25° C.). To the reaction mixture was then added Tetrakis(triphenyl phosphine) Palladium(0) (0.422 gm, 0.365 mmol) at 25° C. and tube was sealed. The reaction mixture was then stirred at 100° C. for 18 hours. The progress of the reaction was monitored by TLC. The reaction mixture was then filtered and washed with ethyl acetate (2×100 ml). The combined organic layer was then concentrated under reduced pressure to obtain a crude product as semi-solid (11.2 gm), which was then purified by column chromatography over silica gel (100-200 mesh) using 50% ethyl acetate in hexanes as an eluent to obtain the title compound (1.2 g, 55.60%)

1. customPrepared
2. customA nitrogen gas was purged to the suspension for 15 minute at room temperature (about 25° C.)
3. filtrationThe reaction mixture was then filtered
4. washwashed with ethyl acetate (2×100 ml)
5. concentrationThe combined organic layer was then concentrated under reduced pressure
6. customto obtain a crude product as semi-solid (11.2 gm), which
7. customwas then purified by column chromatography over silica gel (100-200 mesh)

ORD record

ord-c8982aa8373e472da5be8db211160cca

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09072731B2