Sodium Carbonate → HCID 22324111, compound

HRID 496156Notes

Reaction equation

HRID 496156 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Br)[C:5]([CH3:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=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>[NH2:1][C:2]1[CH:7]=[C:6]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH3:14])[C:5]([CH3:9])=[CH:4][C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 223240412-Amino-4-bromo-5-methylbenzenesulfonamide

Product 1

HCID 22324111HCID 22324111, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Bromo-4-methylaniline was transformed by Method B (The isomers were separated by fractional crystallization from MeOH) to give 2-amino-4-bromo-5-methylbenzenesulfonamide. A mixture of 2-amino-4-bromo-5-methylbenzenesulfonamide (100 mg, 0.38 mmol), 2-methoxyphenylboronic acid (76 mg, 0.50 mmol), Pd(PPh3)2Cl2 (13 mg, 5 mol %) in 1,2-dimethoxyethane (20 ml) and Na2CO3 (2M, 1 ml, 2 mmol) were refluxed under N2 for 4 h. The solvents were removed under reduced pressure and the residue was treated with saturated NaHCO3 (10 ml) and extracted with EtOAc (2×25 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 100 mg (90%) of 2-amino-4-(2-methoxyphenyl)-5-methylbenzenesulfonamide as colorless powder. The product was further transformed by Method G (using cyclohexanecarboxaldehyde). M.p. 172-175° C.

Workup

  1. temperaturewere refluxed under N2 for 4 h
  2. customThe solvents were removed under reduced pressure
  3. additionthe residue was treated with saturated NaHCO3 (10 ml)
  4. extractionextracted with EtOAc (2×25 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-d656dde16a334bd186492bebe792dbf4
Source dataset
uspto-grants-2005_09
Patent number
US06943159B1

Reaction notes

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