Sodium Carbonate → HCID 22723451, compound

HRID 1272204Notes

Reaction equation

HRID 1272204 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.Br[C:13]1[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)CC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[S:17][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 12413045-Bromo-2-thiophenesulfonamideHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 22723451HCID 22723451, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
88 °C

Procedure

A 25 ml 1-propanol solution of 2-methoxyphenyl boronic acid (1.2 g, 7.5 mmol) and 5-bromothien-2-ylsulfonamide (1.2 g, 5 mmol) is stirred under N2 at room temperature. Palladium(II) acetate (56 mg, 0.25 mmol), triphenylphosphine (200 mg, 0.75 mmol), 2M aqueous Na2CO3 (3 ml, 6 mmol), and 7 ml H2O are added and the resulting mixture is refluxed (˜88° C.) for 1 hour. The reaction is cooled, diluted with ethyl acetate, washed with brine, and the brine back extracted with ethyl acetate. The extracts are combined, washed with aqueous NaHCO3, brine, dried (Na2SO4), filtered, and the filtrate is concentrated. The residue is purified by chromatography (SiO2, ethyl acetate/hexane gradient) to give 943 mg (70%) of 5-(2-methoxyphenyl)thiophene-2-sulfonamide.

Workup

  1. temperatureThe reaction is cooled
  2. washwashed with brine
  3. extractionthe brine back extracted with ethyl acetate
  4. washwashed with aqueous NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated
  8. customThe residue is purified by chromatography (SiO2, ethyl acetate/hexane gradient)

Sources & evidence

ORD record
ord-8f33dd70aa894ed99e3d9568e1b29e61
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

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