Sodium Carbonate → HCID 86723252, compound

HRID 1846029Notes

Reaction equation

HRID 1846029 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4](I)[CH:3]=1.[CH3:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:18]2[CH:17]=[CH:16][C:15]([S:12]([NH:11][CH3:10])(=[O:13])=[O:14])=[CH:20][CH:19]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 441187634-((Methylamino)sulphonyl)benzene boronic acid

Product 1

HCID 86723252HCID 86723252, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-bromo-1-fluoro-2-iodobenzene (207 mg, 0.69 mmol) in anhydrous dioxane (3.4 mL) was added [4-(methylsulfamoyl)phenyl]boronic acid (148 mg, 0.69 mmol) and aqueous Na2CO3 solution (2M, 1.03 mL, 2.06 mmol). A stream of nitrogen gas was bubbled through the reaction mixture for 6 minutes. Tetrakistriphenylphosphine palladium(0) (24 mg, 0.021 mmol) was added and the mixture was heated under microwave irradiation at 120° C. for 12 minutes. The reaction mixture was cooled, diluted with EtOAc, treated with anhydrous Na2SO4 and filtered, washing the solids with EtOAc until the compound had completely eluted. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 100:0 to 60:40 to afford the title compound as clear, colorless residue in 67% yield, 159 mg.

Workup

  1. customA stream of nitrogen gas was bubbled through the reaction mixture for 6 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washwashing the solids with EtOAc until the compound
  5. washhad completely eluted
  6. customThe filtrate was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with heptane:EtOAc 100:0 to 60:40

Sources & evidence

ORD record
ord-c79d085c845a427893aa7ddb043b1bfe
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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