4-Bromo-N,N-dimethylbenzenesulphonamide → HCID 68504904, compound

HRID 1711295Notes

Reaction equation

HRID 1711295 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1.C1(C)C=CC=CC=1>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=2)=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 128184-Bromo-N,N-dimethylbenzenesulphonamideHCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27346154-Aminophenylboronic acid

Product 1

HCID 68504904HCID 68504904, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a round bottom flask was added 4-bromo-N,N-dimethyl-benzenesulfonamide (as prepared in the previous step, 539 mg, 2.28 mmol), 4-aminophenylboronic acid (500 mg, 2.28 mmol), Pd(OAc)2 (51 mg, 0.22 mmol), K3PO4 (967 mg, 4.56 mmol) and 2-(dicyclohexyl-phosphino)-biphenyl (319 mg, 0.910 mmol). The flask was charged with toluene (10 mL) and dioxane (10 mL) and heated to 90° C. under Ar. After 5 h the reaction was concentrated in vacuo and the residue was purified by a 10-g silica gel SPE-column eluting with DCM followed by 10% MeOH-DCM to afford 67 mg (10%) of the title compound as a tan solid. Mass spectrum (ESI, m/z): Calcd. for C14H16N2O2S, 277.0 (M+H), found 277.1.

Workup

  1. concentrationAfter 5 h the reaction was concentrated in vacuo
  2. customthe residue was purified by a 10-g silica gel SPE-column
  3. washeluting with DCM

Sources & evidence

ORD record
ord-0f7c6a661aae4636aa18d30fb2bee84c
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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