4-Bromobiphenyl → HCID 18702053, compound

HRID 2288936Notes

Reaction equation

HRID 2288936 reaction equation
[CH3:1][N:2]([CH2:11][CH:12]=[CH2:13])[S:3]([CH2:6][C:7]([O:9][CH3:10])=[O:8])(=[O:5])=[O:4].Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:10][O:9][C:7](=[O:8])[CH2:6][S:3]([N:2]([CH3:1])[CH2:11]/[CH:12]=[CH:13]/[C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=2)=[CH:22][CH:23]=1)(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 71014-BromobiphenylHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 18702051HCID 18702051, compound

Product 1

HCID 18702053HCID 18702053, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-({methyl[allyl]amino}sulfonyl)acetate (300 mg, 1.4 mmol) and 4-bromobiphenyl (370 mg, 1.54 mmol) in acetonitrile (4 ml) was added triethylamine (0.3 ml, 2.1 mmol), palladium(II) acetate (17 mg, 0.07 mmol) and tri-ortho-tolyl phosphine (52 mg, 0.14 mmol) and the solution was heated to reflux under an atmosphere of nitrogen for 3 hours. The mixture was cooled to ambient temperature, the solvent was evaporated and the residue was purified by flash chromatography on silica gel (dichloromethane as eluent) to give the title compound as a pale yellow solid (300 mg).

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux under an atmosphere of nitrogen for 3 hours
  3. customthe solvent was evaporated
  4. customthe residue was purified by flash chromatography on silica gel (dichloromethane as eluent)

Sources & evidence

ORD record
ord-018a978672d641d08337a5eefda3d022
Source dataset
uspto-grants-2000_07
Patent number
US06090852

Reaction notes

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