Water → N-tert-butyl-4'-aminobiphenyl-2-sulfonamide

HRID 2184897Notes

Reaction equation

HRID 2184897 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Na+].Br[C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)(C)C>[NH2:26][C:25]1[CH:27]=[CH:28][C:22]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 962WaterHCID 78074-BromoanilineHCID 14798Sodium HydroxideHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-

Product 1

HCID 10804475N-tert-butyl-4'-aminobiphenyl-2-sulfonamide

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 2-[(tert-butyl amino)sulfonyl]phenyl boronic acid (6.00 g, 23.35 mmol) in 120 ml toluene was added water (16 ml), isopropanol (60 ml), and NaOH (40 ml, 5M aqueous solution). To this were added 4-bromoaniline and Pd(Ph3P)4. This heterogeneous mixture is then refluxed for 6 hr, then stirred at room temperature over night before refluxing for another 1.5 hr. The reaction mixture is then extracted with water and ethyl acetate. The aqueous layer is extracted twice with ethyl acetate. The organic layers are then dried over MgSO4, filtered and concentrated in vacuo. The crude residue is purified by silica gel flash chromatography. The desired product can be eluded with 30% ethyl acetate in hexanes and concentrated to an orange solid (5.06 g, 16.65, 71%). ES-MS(M+H)+=305.

Workup

  1. temperatureThis heterogeneous mixture is then refluxed for 6 hr
  2. temperaturebefore refluxing for another 1.5 hr
  3. extractionThe reaction mixture is then extracted with water and ethyl acetate
  4. extractionThe aqueous layer is extracted twice with ethyl acetate
  5. dry with materialThe organic layers are then dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue is purified by silica gel flash chromatography
  9. concentrationconcentrated to an orange solid (5.06 g, 16.65, 71%)

Sources & evidence

ORD record
ord-bcccea36aa9742b2b3de1585fd020e06
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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