Sodium Carbonate → HCID 22324046, compound

HRID 1767608Notes

Reaction equation

HRID 1767608 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:4]([NH2:12])[CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[NH2:12][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][CH3:13])[CH:7]=[CH:6][C:5]=1[S:8]([NH2:11])(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 1245249554734-81-5

Product 1

HCID 22324046HCID 22324046, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-bromo-2-aminobenzenesulfonamide (140 mg, 0.56 mmol), 2-methoxyphenylboronic acid (106 mg, 0.70 mmol), Pd(PPh3)2Cl2 (20 mg, 5 mol %) in 1,2-dimethoxyethane (30 ml) and Na2CO3 (2M, 3 ml, 6 mmol) was refluxed under N2 for 4 h. The solvents were removed under reduced pressure and the residue was treated with saturated NaHCO3 (20 ml) and extracted with EtOAc (2×40 ml). The organic layer was washed with brine (20 ml), dried (Na2SO4) and the solvent was removed under reduced pressure. The product was purified by flash chromatography on SiO2 using EtOAc:n-hexane (1:1, v/v) as eluent, yielding 155 mg (100%) of 2-amino-4-(2-methoxyphenyl)-benzenesulfonamide as colorless powder. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 219–221° C.

Workup

  1. temperaturewas refluxed under N2 for 4 h
  2. customThe solvents were removed under reduced pressure
  3. additionthe residue was treated with saturated NaHCO3 (20 ml)
  4. extractionextracted with EtOAc (2×40 ml)
  5. washThe organic layer was washed with brine (20 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent was removed under reduced pressure
  8. customThe product was purified by flash chromatography on SiO2

Sources & evidence

ORD record
ord-5fd3a4003e12454cad4381757101f376
Source dataset
uspto-grants-2007_06
Patent number
US07235548B2

Reaction notes

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