Sodium Carbonate → HCID 86723228, compound

HRID 1845996Notes

Reaction equation

HRID 1845996 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4](I)[CH:3]=1.[S:10]([C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1)(=[O:13])(=[O:12])[NH2:11].O1CCOCC1.O.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:17]2[CH:18]=[CH:19][C:14]([S:10]([NH2:11])(=[O:13])=[O:12])=[CH:15][CH:16]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 218864351,4-Dioxane--water (1/1)HCID 223919774-(Aminosulphonyl)benzeneboronic acid

Product 1

HCID 86723228HCID 86723228, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To 4-bromo-1-fluoro-2-iodobenzene (361 mg, 1.2 mmol) and 4-sulfamoyl-phenylboronic acid (240 mg, 1.20 mmol) in 4:1 dioxane/H2O (5 mL) was added Na2CO3 (382 mg, 3.60 mmol) and [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (34.3 mg, 0.042 mmol). The reaction was heated under microwave irradiation at 120° C. for 15 minutes, cooled and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layers dried over Na2SO4. The solvent was removed in vacuo and the resulting residue purified via silica gel column chromatography eluting with EtOAc:heptanes 0:1 to 1:1 to afford the desired product 55%, 218 mg, 55%.

Workup

  1. temperaturecooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers dried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe resulting residue purified via silica gel column chromatography
  6. washeluting with EtOAc:heptanes 0:1 to 1:1

Sources & evidence

ORD record
ord-548cb92f46994c4a9aa5a5f988ec693a
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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