Sodium Chloride → HCID 58597404, compound

HRID 2224624Notes

Reaction equation

HRID 2224624 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)(=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>C(COC)OC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(=[O:22])[CH3:21]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 846804HCID 846804, compoundHCID 27343092-Acetylphenylboronic acid

Product 1

HCID 58597404HCID 58597404, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

N-(2-Bromo-phenyl)4-methoxy-benzenesulfonamide (0.34 g, 0.99 mmol) was dissolved in dimethoxyethane (4 mL) and tetrakis(triphenylphosphine)palladium (0) (0.23 g, 0.2 mmol) was added. 2-acetylphenylboronic acid (0.16 g, 0.99 mmol), dissolved in ethanol (1 mL), was added, followed by aqueous sodium carbonate (4.2 mL, 2 M). The reaction mixture was heated at 100° C. for 14 hours. The mixture was diluted with a saturated, aqueous sodium chloride solution (200 mL) and extracted with dichloromethane (4×30 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield a residue. The crude product was purified by silica gel chromatography (1:9 to 3:7 ethyl acetate:hexane) to afford the title product.

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane (4×30 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a residue
  7. customThe crude product was purified by silica gel chromatography (1:9 to 3:7 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-1066034688d24fc78cc08de6091f2026
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

Loading…