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

HRID 2425137Notes

Reaction equation

HRID 2425137 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)(=[O:9])=[O:8].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:29])([F:28])[F:17])=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 160947204-Bromo-N-(4-hydroxybutyl)benzene-1-sulfonamide

Product 1

HCID 11682252[1,1'-Biphenyl]-4-sulfonamide, N-(4-hydroxybutyl)-4'-(trifluoromethyl)-

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-98d38c81eaae43b1b7b712a4538acfe8
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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