Cesium carbonate → N-(2,4-dimethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide

HRID 1487040Notes

Reaction equation

HRID 1487040 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[CH3:23])[CH2:12][CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B-](F)(F)(F)[CH:25]=[CH2:26].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>ClCCl.[Pd](Cl)Cl.C(OCC)(=O)C.O.O1CCCC1>[CH3:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:25]=[CH2:26])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

10

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 23679353Potassium vinyltrifluoroborateHCID 867315904-bromo-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide

Product 1

HCID 86731589N-(2,4-dimethylphenyl)-N-isobutyl-4-vinylbenzenesulfonamide

Reagents, catalysts & solvents 5

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave vial was added 4-bromo-N-(2,4-dimethylphenyl)-N-isobutylbenzenesulfonamide (4.44 g, 11.20 mmol), potassium trifluoro(vinyl)borate (4.50 g, 33.6 mmol), triphenylphosphine (0.176 g, 0.672 mmol), cesium carbonate (10.95 g, 33.6 mmol) and palladium(II) chloride (0.040 g, 0.224 mmol). Tetrahydrofuran (THF) (12 mL) and water (1.333 mL) were then added, ensuring all particles were below the solvent level. The reaction vessel was sealed and heated in a microwave (Biotage Initiator) to 140° C. for 60 minutes, cooled to room temperature and ethyl acetate (40 mL) added to the mixture. The organic phase was washed with water (50 mL), dried using a hydrophobic frit and evaporated in vacuo to give the crude product as a orange oil. The sample was loaded in dichloromethane and purified by silica (Si) chromatography using a 0-25% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product, 1.8 g, as an off-white solid. LCMS [LCMS1] Rt 1.47 min, m/z (ES+) 344 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temperature
  3. washThe organic phase was washed with water (50 mL)
  4. customdried
  5. customevaporated in vacuo
  6. customto give the crude product as a orange oil
  7. custompurified by silica (Si) chromatography
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-322f9b6807404aa6835789b0bb60c507
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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