Dimethylformamide → HCID 10293862, compound

HRID 1072685Notes

Reaction equation

HRID 1072685 reaction equation
Br[C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]([CH3:16])[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[CH:4][CH:3]=1.[C:19]([O-])(=O)[CH3:20].[K+].CN(C)[CH:26]=[O:27].[C:29](=[O:32])([O-])[O-].[Na+].[Na+]>C(OCC)C>[CH3:16][CH:7]([O:6][C:5]1[CH:17]=[CH:18][C:2]([C:20]2[CH:19]=[CH:4][C:3]([C:29]([O:27][CH3:26])=[O:32])=[CH:2][CH:18]=2)=[CH:3][CH:4]=1)[CH2:8][NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 9840705HCID 9840705, compound

Product 1

HCID 10293862HCID 10293862, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

[2-(4-Bromophenoxy)propyl][(methylethyl)sulfonyl]amine (500 mg, 1.487 mmol) was combined with bis(pinicolato)diboron (415 mg, 1.636 mmol), potassium acetate (440 mg, 4.461 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride complex (0.045 mmol) and dimethylformamide (10 mL) in a 3-neck round bottomed flask fitted with a thermometer, stirbar, condenser, and in a nitrogen system. This reaction mixture was refluxed to 80° C. with stirring, for three hours. The reaction mixture was cooled to room temperature, and [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride complex (0.045 mmol) was added, followed by 2M sodium carbonate (3.7 mL), and refluxed to 80° C., with stirring, overnight. The reaction was cooled to room temperature, and diluted with 100 mL of diethyl ether, and washed with 100 mL water and 100 mL brine. Organic layer was dried with potassium carbonate, filtered and concentrated in-vacuo, yielding 1.53 g of brown solid. This material was further purified using a 6000 uM rotor on a Chromatotron in a 1:1 hexanes:ethyl acetate solvent system to provide the title compound (50 mg, 9%) as yellow crystals.

Workup

  1. customfitted with a thermometer, stirbar, condenser
  2. temperatureThe reaction mixture was cooled to room temperature
  3. addition[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride complex (0.045 mmol) was added
  4. temperaturerefluxed to 80° C.
  5. stirringwith stirring, overnight
  6. temperatureThe reaction was cooled to room temperature
  7. washwashed with 100 mL water and 100 mL brine
  8. dry with materialOrganic layer was dried with potassium carbonate
  9. filtrationfiltered
  10. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-17da9c3f3514488eb8e664d1b56cc31c
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

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