Sodium Carbonate → HCID 9969257, compound

HRID 1072657Notes

Reaction equation

HRID 1072657 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.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[Cl:19][C:20]1[CH:25]=[C:24]([C:2]2[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]=2)[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 9840705HCID 9840705, compound

Product 1

HCID 9969257HCID 9969257, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

[2-(4-Bromophenoxy)propyl][(methylethyl)sulfonyl]amine (300 mg, 0.892 mmol, prepared in example 1), 3-chlorobenzeneboronic acid (170 mg, 1.09 mmol), dichlorobis(triphenylphosphine)palladium(II) (25 mg, 0.036 mmol), 2 M sodium carbonate (320 mg in 1.5 mL water) and 1,2-dimethoxyethane (6.0 mL) were combined in a 15 ml round bottom flask, fitted with a condenser, stirbar, and in a temperature regulated oil bath, and heated at reflux 85 C. in a nitrogen system overnight. The reaction mixture was quenched with water and extracted three times with 25 mL of methylene chloride. The organic extracts were combined, dried over anyhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, yielding 190 mg brown viscous oil. This material was purified via silica gel chromatography, utilizing a Chromatotron® with a 2000 μm rotor in a 1:1 hexane:ethyl acetate solvent system, yielding the title compound (175 mg, 53%) as a yellow foam. Electrospray-MS 369.0 (M*+1).

Workup

  1. customfitted with a condenser
  2. temperatureheated
  3. temperatureat reflux 85 C
  4. customin a nitrogen system overnight
  5. customThe reaction mixture was quenched with water
  6. extractionextracted three times with 25 mL of methylene chloride
  7. dry with materialdried over anyhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2bd3ba06929493c9bdede1d5e532c72
Source dataset
uspto-grants-2005_06
Patent number
US06911476B2

Reaction notes

Loading…