Sodium Carbonate → [1,1'-Biphenyl]-4-sulfonamide, N-(4-hydroxybutyl)-4'-(trifluoromethyl)-

4-Bromophenyl-sulfonic acid-(4-hydroxybutyl)-amide (1 g) was dissolved in ethanol (8 mL) and toluene (8 mL). 4-Trifluoromethylphenyl boronic acid (1 g) was added, followed by 2 M Na2CO3 (8 mL). Tetrakis(triphenylphosphine) palladium (0.25 g) was added and the mixture heated to reflux under nitrogen for 3 hours with vigorous stirring. The organic solvents were evaporated and the residue dissolved in ethyl acetate (100 mL) and washed with water (100 mL) then saturated NaCl solution (100 mL). The organic phase was dried (Na2SO4), evaporated and the residue purified by column chromatography (ethyl acetate/petrol) to give the title compound as a white solid. δC (DMSO, 62.9 MHz): 25.9, 29.6, 42.6, 60.2, indistinct m, 140.4, 142.2 and 142.6. δH (DMSO, 250 MHz): 1.41 (4H, m), 2.77 (2H, m), 3.33 (2H, m), 4.39 (1H, t, NH), 7.83-7.94 (6 H, m) and 7.96 (2H, d, J 8.5).

1. temperaturethe mixture heated
2. temperatureto reflux under nitrogen for 3 hours with vigorous stirring
3. customThe organic solvents were evaporated
4. dissolutionthe residue dissolved in ethyl acetate (100 mL)
5. washwashed with water (100 mL)
6. dry with materialThe organic phase was dried (Na2SO4)
7. customevaporated
8. customthe residue purified by column chromatography (ethyl acetate/petrol)

ORD record

ord-98d38c81eaae43b1b7b712a4538acfe8

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964643B2